Efficient one-pot synthesis of substituted 2-amino-1,3,4-oxadiazoles

A convenient one-pot method for the preparation of substituted 2-amino-1,3,4-oxadiazoles is described. A convenient one-pot method for the preparation of substituted 2-amino-1,3,4-oxadiazoles has been developed. The method is a significant improvement over previously reported syntheses. Reaction of...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron letters Vol. 49; no. 47; pp. 6709 - 6711
Main Authors Piatnitski Chekler, Eugene L., Elokdah, Hassan M., Butera, John
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 17.11.2008
Elsevier
Subjects
Online AccessGet full text

Cover

Loading…
Abstract A convenient one-pot method for the preparation of substituted 2-amino-1,3,4-oxadiazoles is described. A convenient one-pot method for the preparation of substituted 2-amino-1,3,4-oxadiazoles has been developed. The method is a significant improvement over previously reported syntheses. Reaction of carboxylic acids with thiosemicarbazides afforded the corresponding oxadiazoles in moderate to good yields. In general, the products precipitated from the reaction mixture, and were collected by filtration. In most of the cases, no chromatographic separations were required. To explore the scope and limitations of this reaction, various aliphatic, aromatic, and heteroaromatic carboxylic acids were reacted with different substituted thiosemicarbazides. The influence of R 1 and R 2 substituents on the reaction yield and additional results demonstrating the versatility of this method are presented.
AbstractList A convenient one-pot method for the preparation of substituted 2-amino-1,3,4-oxadiazoles has been developed. The method is a significant improvement over previously reported syntheses. Reaction of carboxylic acids with thiosemicarbazides afforded the corresponding oxadiazoles in moderate to good yields. In general, the products precipitated from the reaction mixture, and were collected by filtration. In most of the cases, no chromatographic separations were required. To explore the scope and limitations of this reaction, various aliphatic, aromatic, and heteroaromatic carboxylic acids were reacted with different substituted thiosemicarbazides. The influence of R-1 and R-2 substituents on the reaction yield and additional results demonstrating the versatility of this method are presented. (c) 2008 Elsevier Ltd. All rights reserved.
A convenient one-pot method for the preparation of substituted 2-amino-1,3,4-oxadiazoles is described. A convenient one-pot method for the preparation of substituted 2-amino-1,3,4-oxadiazoles has been developed. The method is a significant improvement over previously reported syntheses. Reaction of carboxylic acids with thiosemicarbazides afforded the corresponding oxadiazoles in moderate to good yields. In general, the products precipitated from the reaction mixture, and were collected by filtration. In most of the cases, no chromatographic separations were required. To explore the scope and limitations of this reaction, various aliphatic, aromatic, and heteroaromatic carboxylic acids were reacted with different substituted thiosemicarbazides. The influence of R 1 and R 2 substituents on the reaction yield and additional results demonstrating the versatility of this method are presented.
Author Butera, John
Piatnitski Chekler, Eugene L.
Elokdah, Hassan M.
Author_xml – sequence: 1
  givenname: Eugene L.
  surname: Piatnitski Chekler
  fullname: Piatnitski Chekler, Eugene L.
  email: piatnits@gmail.com
– sequence: 2
  givenname: Hassan M.
  surname: Elokdah
  fullname: Elokdah, Hassan M.
– sequence: 3
  givenname: John
  surname: Butera
  fullname: Butera, John
BookMark eNqNkE1LAzEQhoNUsFb_gYe926yzm_3KRZC1fkDBi55Dmkwwpd2UTarWX2-WLR7Fucwc3meYec7JpHMdEnKVQZpBVt2s04BhgyHNAZoUeAplfUKmWVMzysomm5ApQAG0AMbPyLn3a4hVNTAl9wtjrLLYhSTupDsXEn_owjt66xNnEr9f-WDDPqBOciq3tnM0m7N5Qd2X1FZ-uw36C3Jq5Mbj5bHPyNvD4rV9osuXx-f2bkkVgyrQKlsxKMoaecVZCZzLuqmwZHmt8loqjXkjOVO6MVIrrYwsNRRMIZclU6VhbEaKca_qnfc9GrHr7Vb2B5GBGEyItRhNiMGEAC6iiYg1I_aJK2f88K3CXzSayCvgRcGHibc2yGBd17p9FyJ6_X80pm_HNEYJHxZ7cSS07VEFoZ39-9IfspCL3Q
CitedBy_id crossref_primary_10_1016_j_tetlet_2012_05_154
crossref_primary_10_1039_c3ra41044g
crossref_primary_10_1080_00304948_2017_1342511
crossref_primary_10_1007_s11030_021_10367_4
crossref_primary_10_1016_j_tet_2011_05_100
crossref_primary_10_1039_c3ra46916f
crossref_primary_10_1080_00397911_2013_879901
crossref_primary_10_1016_j_tetlet_2010_09_122
crossref_primary_10_1002_adsc_201200408
crossref_primary_10_2174_1570178619666211231110106
crossref_primary_10_1039_C4RA11218K
crossref_primary_10_1039_c3ra21904f
crossref_primary_10_2174_1570193X19666220112151214
crossref_primary_10_1021_jo2025509
crossref_primary_10_1021_acscombsci_8b00044
crossref_primary_10_1134_S1068162015020089
crossref_primary_10_1002_ardp_202400185
crossref_primary_10_1007_s12039_015_0834_x
crossref_primary_10_1016_j_tetlet_2023_154548
crossref_primary_10_1039_C7NJ04720G
crossref_primary_10_1002_chin_200910122
crossref_primary_10_19261_cjm_2022_1026
crossref_primary_10_1016_j_tet_2012_11_071
crossref_primary_10_1021_jm100941j
crossref_primary_10_1039_C7NJ02278F
crossref_primary_10_1039_c2ra00044j
crossref_primary_10_1021_jm400830r
crossref_primary_10_1016_j_arabjc_2022_103712
crossref_primary_10_1016_j_tet_2021_132382
crossref_primary_10_1002_mabi_201600221
crossref_primary_10_1016_j_tetlet_2018_06_068
crossref_primary_10_1515_cse_2015_0009
crossref_primary_10_1016_j_molstruc_2024_138563
Cites_doi 10.1016/j.tetlet.2004.02.119
10.1016/j.bmcl.2006.01.119
10.1016/j.tet.2005.03.062
10.1021/jo0618730
10.1016/j.tet.2006.01.054
10.1002/mrc.1928
10.1016/j.bmcl.2005.11.094
10.1055/s-2001-11404
10.1016/0223-5234(96)83976-6
10.1002/prac.19693110403
10.1002/hc.20071
ContentType Journal Article
Copyright 2008 Elsevier Ltd
Copyright_xml – notice: 2008 Elsevier Ltd
DBID 1KN
BLEPL
DTL
GAYFB
AAYXX
CITATION
DOI 10.1016/j.tetlet.2008.09.057
DatabaseName Current Chemical Reactions
Web of Science Core Collection
Science Citation Index Expanded
Web of Science - Science Citation Index Expanded - 2008
CrossRef
DatabaseTitle Web of Science
CrossRef
DatabaseTitleList Web of Science

Database_xml – sequence: 1
  dbid: 1KN
  name: Current Chemical Reactions
  url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/woscc/search-with-editions?editions=WOS.CCR
  sourceTypes:
    Enrichment Source
    Index Database
DeliveryMethod fulltext_linktorsrc
Discipline Chemistry
EISSN 1873-3581
EndPage 6711
ExternalDocumentID 10_1016_j_tetlet_2008_09_057
000260944900029
S0040403908017152
GroupedDBID ---
--K
--M
-ET
-~X
.GJ
.HR
.~1
0R~
123
186
1B1
1RT
1~.
1~5
29Q
3EH
4.4
457
4G.
53G
5VS
6TJ
7-5
71M
85S
8P~
9JM
9JN
AABNK
AACTN
AAEDT
AAEDW
AAIAV
AAIKJ
AAKOC
AALRI
AAOAW
AAQFI
AAQXK
AARLI
AATCM
AAXUO
AAYOK
ABFNM
ABFRF
ABGSF
ABJNI
ABMAC
ABPPZ
ABUDA
ABXDB
ABYKQ
ABZDS
ACBEA
ACBNA
ACDAQ
ACGFS
ACKIV
ACNCT
ACNNM
ACRLP
ADBBV
ADECG
ADEZE
ADMUD
ADUVX
AEBSH
AEFWE
AEHWI
AEKER
AENEX
AFFNX
AFKWA
AFMIJ
AFTJW
AFXIZ
AFZHZ
AGHFR
AGRDE
AGUBO
AGYEJ
AHHHB
AIEXJ
AIKHN
AITUG
AJBFU
AJOXV
AJSZI
ALCLG
ALMA_UNASSIGNED_HOLDINGS
AMFUW
AMRAJ
ASPBG
AVWKF
AXJTR
AZFZN
BKOJK
BLXMC
CS3
D0S
DOVZS
DU5
EBS
EFJIC
EFLBG
EJD
EO8
EO9
EP2
EP3
F5P
FDB
FEDTE
FGOYB
FIRID
FLBIZ
FNPLU
FYGXN
G-Q
G8K
GBLVA
HMS
HVGLF
HZ~
IH2
IHE
J1W
K-O
KOM
M2Z
M41
MO0
MVM
N9A
O-L
O9-
OAUVE
OGGZJ
OHT
OZT
P-8
P-9
P2P
PC.
Q38
R2-
RIG
RNS
ROL
RPZ
SCB
SCC
SDF
SDG
SDP
SES
SEW
SOC
SPC
SPCBC
SSK
SSP
SSU
SSZ
T5K
TN5
TWZ
UQL
WH7
WUQ
XFK
XJT
XPP
XSW
Y6R
YK3
YQJ
YR2
ZCG
ZKB
ZMT
ZXP
~02
~G-
~KM
1KN
AAHBH
AAXKI
ADVLN
AKRWK
BLEPL
DTL
GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED
AAYXX
AFJKZ
CITATION
ID FETCH-LOGICAL-c306t-61b30457e96935099a786e5327c27acde28a93cd8fadcdcfa5d043ce9a53c5f33
IEDL.DBID AIKHN
ISICitedReferencesCount 40
ISICitedReferencesURI https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000260944900029
ISSN 0040-4039
IngestDate Thu Sep 26 15:33:01 EDT 2024
Tue Sep 17 23:21:01 EDT 2024
Fri Oct 11 20:04:40 EDT 2024
Fri Feb 23 02:29:24 EST 2024
IsPeerReviewed true
IsScholarly true
Issue 47
Keywords Oxadiazole
Kinase inhibitor
One-pot cyclization
ACID
DERIVATIVES
Language English
LinkModel DirectLink
LogoURL https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg
MergedId FETCHMERGED-LOGICAL-c306t-61b30457e96935099a786e5327c27acde28a93cd8fadcdcfa5d043ce9a53c5f33
PageCount 3
ParticipantIDs elsevier_sciencedirect_doi_10_1016_j_tetlet_2008_09_057
webofscience_primary_000260944900029CitationCount
crossref_primary_10_1016_j_tetlet_2008_09_057
webofscience_primary_000260944900029
PublicationCentury 2000
PublicationDate 2008-11-17
PublicationDateYYYYMMDD 2008-11-17
PublicationDate_xml – month: 11
  year: 2008
  text: 2008-11-17
  day: 17
PublicationDecade 2000
PublicationPlace OXFORD
PublicationPlace_xml – name: OXFORD
PublicationTitle Tetrahedron letters
PublicationTitleAbbrev TETRAHEDRON LETT
PublicationYear 2008
Publisher Elsevier Ltd
Elsevier
Publisher_xml – name: Elsevier Ltd
– name: Elsevier
References Biwersi, C. M.; Warmus, J. S.; Zhang, L. Y.; Barrett, S. D.; Kaufman, M. D.; Plummer, M. S.; Reed, J. E. WO 2004056789, 2004.
Simiti, Ghiran (bib18) 1971; 19
Blouin, M.; Grimm, E. L.; Gareau, Y.; Gagnon, M.; Juteau, H.; Laliberte, S.; Mackay, B.; Friesen, R. WO 2006099735, 2006.
Baxendale, Ley, Martinelli (bib19) 2005; 61
Piatnitski, E. L.; Kiselyov, A. S.; Doody, J.; Hadari, Y. R.; Ouyang, S.; Chen, X. WO 2004052280, 2004.
Black, S. L.; Kaufman, M. D.; Ortwine, D. F.; Plummer, M. S.; Quin, J.; Rewcastle, G. W.; Shahripour, A. B.; Spicer, J. A.; Whitehead, C. E. WO 2005000818, 2005.
Bilinski, Bielak, Chmielewski, Marcewicz-Rojewska, Musik (bib16) 1989; 46
Gumien (bib9) 1983; 30
Marcewicz-Rojewska, Bilinski (bib8) 1980; 37
Coppo, Evans, Graybill, Burton (bib15) 2004; 45
Hassan, El-Shaieb, Shaker, Doepp (bib5) 2005; 16
Madhavan, Srinivasan (bib6) 1969; 7
Sawhney, Singh, Bansal (bib10) 1975; 13
Birch, A. M.; Bowker, S. S.; Butlin, R. J.; Donald, C. S.; McCoull, W.; Nowak, T.; Plowright, A. WO 2006064189, 2006.
Ouyang, Piatnitski, Pattaropong, Chen, He, Kiselyov, Velankar, Kawakami, Labelle, Smith, Lohman, Lee, Malikzay, Fleming, Gerlak, Wang, Rosler, Zhou, Mitelman, Camara, Surguladze, Doody, Tuma, Hiremath, Biradar, Kudari (bib3) 2006; 16
Brain, Brunton (bib21) 2001
Barth, F.; Congy, C.; Gueule, P.; Rinaldi-Carmona, M.; Van Broeck, D. WO 2006087480, 2006.
Omar, Mahfouz, Rahman (bib7) 1996; 31
Dehuri, Pradhan, Nayak (bib13) 1983; 22B
Gierczyk, Nowak-Wydra, Grajewski, Zalas (bib17) 2007; 45
Gehlen, Drohla (bib20) 1969; 311
Leber, J. D.; Li, M.; Lee, J.; Aubart, K. M.; Christensen, S. B. WO 2005032550, 2005.
226th ACS National Meeting, 2003.
Dehuri, Pradhan, Nayak (bib14) 1983; 60
Kelarev, Shvekhgeimer, Lunin (bib12) 1984
Dumciute, Martynaitis, Holzer, Mangelinckx, De Kimpe, Sackus, Amir, Kumar, Dolman, Gosselin, O’Shea, Davies (bib4) 2006; 62
Hiremath, Bajji, Biradar (bib11) 1992; 62
Handlon, A. L.; Akwabi-Ameyaw, A.; Brown, K.; De Anda, F.; Drewry, D.; Fang, J.; Irsula, O.; Li, G.; Linn, J. A.; Milliken, N. O.; Ramanjulu, J.
(WOS:000260944900029.1) 2006
(WOS:000260944900029.6) 2004
Baxendale, IR (WOS:000229484400016) 2005; 61
Gierczyk, B (WOS:000243695200004) 2007; 45
Dolman, SJ (WOS:000242426900046) 2006; 71
DEHURI, SN (WOS:A1983RM93100028) 1983; 22
HIREMATH SP (WOS:000260944900029.23) 1992; 62
(WOS:000260944900029.4) 2005
Dumciute, J (WOS:000236486100013) 2006; 62
MARCEWICZROJEWSKA, B (WOS:A1980KC89600004) 1980; 37
GUMIEN D (WOS:000260944900029.19) 1983; 30
GEHLEN, H (WOS:A1969E332900002) 1969; 311
Omar, FA (WOS:A1996VM47400009) 1996; 31
(WOS:000260944900029.7) 2006
SAWHNEY, SN (WOS:A1975AP52800013) 1975; 13
HIREMATH, SP (WOS:A1984SS88800017) 1984; 61
(WOS:000260944900029.2) 2006
Biliski, S (MEDLINE:2517572) 1989; 46
KELZUEV VI (WOS:000260944900029.24) 1984
Coppo, FT (WOS:000220680400020) 2004; 45
Ouyang, XH (WOS:000235284700019) 2006; 16
Amir, M (WOS:000227746500003) 2005; 60
SIMITI I (WOS:000260944900029.31) 1971; 19
HANDLON AL (WOS:000260944900029.20) 2003
MADHAVAN, R (WOS:A1969E050000007) 1969; 7
(WOS:000260944900029.3) 2005
Hassan, AA (WOS:000226267600003) 2005; 16
Brain, CT (WOS:000167476000017) 2001
(WOS:000260944900029.5) 2004
DEHURI, SN (WOS:A1983RH79500018) 1983; 60
Kiselyov, AS (WOS:000236564500052) 2006; 16
Gehlen (10.1016/j.tetlet.2008.09.057_bib20) 1969; 311
Dolman (10.1016/j.tetlet.2008.09.057_bib4_3) 2006; 25
Kiselyov (10.1016/j.tetlet.2008.09.057_bib2b) 2006; 16
Madhavan (10.1016/j.tetlet.2008.09.057_bib6) 1969; 7
Hiremath (10.1016/j.tetlet.2008.09.057_bib3_2) 1984; 61
Brain (10.1016/j.tetlet.2008.09.057_bib21) 2001
Coppo (10.1016/j.tetlet.2008.09.057_bib15) 2004; 45
Hassan (10.1016/j.tetlet.2008.09.057_bib5) 2005; 16
Gumien (10.1016/j.tetlet.2008.09.057_bib9) 1983; 30
10.1016/j.tetlet.2008.09.057_bib1e
Dehuri (10.1016/j.tetlet.2008.09.057_bib14) 1983; 60
Amir (10.1016/j.tetlet.2008.09.057_bib4_2) 2005; 60
Simiti (10.1016/j.tetlet.2008.09.057_bib18) 1971; 19
Omar (10.1016/j.tetlet.2008.09.057_bib7) 1996; 31
Dumciute (10.1016/j.tetlet.2008.09.057_bib4_1) 2006; 62
Baxendale (10.1016/j.tetlet.2008.09.057_bib19) 2005; 61
Dehuri (10.1016/j.tetlet.2008.09.057_bib13) 1983; 22B
Madhavan (10.1016/j.tetlet.2008.09.057_bib1_6) 1969; 7
Hiremath (10.1016/j.tetlet.2008.09.057_bib11) 1992; 62
Gierczyk (10.1016/j.tetlet.2008.09.057_bib17) 2007; 45
10.1016/j.tetlet.2008.09.057_bib2c
10.1016/j.tetlet.2008.09.057_bib2_4
Sawhney (10.1016/j.tetlet.2008.09.057_bib10) 1975; 13
10.1016/j.tetlet.2008.09.057_bib1_4
Marcewicz-Rojewska (10.1016/j.tetlet.2008.09.057_bib8) 1980; 37
10.1016/j.tetlet.2008.09.057_bib1_3
10.1016/j.tetlet.2008.09.057_bib1_2
10.1016/j.tetlet.2008.09.057_bib2_1
Bilinski (10.1016/j.tetlet.2008.09.057_bib16) 1989; 46
10.1016/j.tetlet.2008.09.057_bib1_1
Ouyang (10.1016/j.tetlet.2008.09.057_bib3a) 2006; 16
Kelarev (10.1016/j.tetlet.2008.09.057_bib12) 1984
References_xml – volume: 37
  start-page: 159
  year: 1980
  end-page: 167
  ident: bib8
  publication-title: Acta Pol. Pharm.
  contributor:
    fullname: Bilinski
– volume: 311
  start-page: 539
  year: 1969
  end-page: 548
  ident: bib20
  publication-title: J. Prakt. Chem. (Leipzig)
  contributor:
    fullname: Drohla
– volume: 7
  start-page: 760
  year: 1969
  end-page: 765
  ident: bib6
  publication-title: Indian J. Chem.
  contributor:
    fullname: Srinivasan
– volume: 31
  start-page: 819
  year: 1996
  end-page: 825
  ident: bib7
  publication-title: Eur. J. Med. Chem.
  contributor:
    fullname: Rahman
– volume: 19
  start-page: 199
  year: 1971
  end-page: 205
  ident: bib18
  publication-title: Farmacia (Bucharest, Romania)
  contributor:
    fullname: Ghiran
– volume: 45
  start-page: 3257
  year: 2004
  end-page: 3260
  ident: bib15
  publication-title: Tetrahedron Lett.
  contributor:
    fullname: Burton
– volume: 30
  start-page: 179
  year: 1983
  end-page: 186
  ident: bib9
  publication-title: Biuletyn Informacyjny Instytutu Lekow
  contributor:
    fullname: Gumien
– volume: 16
  start-page: 12
  year: 2005
  ident: bib5
  publication-title: Heteroat. Chem.
  contributor:
    fullname: Doepp
– volume: 46
  start-page: 343
  year: 1989
  end-page: 349
  ident: bib16
  publication-title: Acta Pol. Pharm.
  contributor:
    fullname: Musik
– volume: 45
  start-page: 123
  year: 2007
  end-page: 127
  ident: bib17
  publication-title: Magn. Reson. Chem.
  contributor:
    fullname: Zalas
– start-page: 1271
  year: 1984
  end-page: 1276
  ident: bib12
  publication-title: Khim. Geterotsikl.
  contributor:
    fullname: Lunin
– volume: 61
  start-page: 5323
  year: 2005
  end-page: 5349
  ident: bib19
  publication-title: Tetrahedron
  contributor:
    fullname: Martinelli
– start-page: 382
  year: 2001
  end-page: 384
  ident: bib21
  publication-title: Synlett
  contributor:
    fullname: Brunton
– volume: 13
  start-page: 804
  year: 1975
  end-page: 807
  ident: bib10
  publication-title: Indian J. Chem.
  contributor:
    fullname: Bansal
– volume: 62
  start-page: 3309
  year: 2006
  end-page: 9551
  ident: bib4
  publication-title: Tetrahedron
  contributor:
    fullname: Davies
– volume: 22B
  start-page: 815
  year: 1983
  end-page: 816
  ident: bib13
  publication-title: Indian J. Chem. Sect. B: Org. Chem. Including Med. Chem.
  contributor:
    fullname: Nayak
– volume: 16
  start-page: 1191
  year: 2006
  end-page: 1196
  ident: bib3
  publication-title: Bioorg. Med. Chem. Lett.
  contributor:
    fullname: Kudari
– volume: 60
  start-page: 475
  year: 1983
  end-page: 478
  ident: bib14
  publication-title: J. Indian Chem. Soc.
  contributor:
    fullname: Nayak
– volume: 62
  start-page: 161
  year: 1992
  end-page: 166
  ident: bib11
  publication-title: Proc. Natl. Acad. Sci., India Sec. A: Phys. Sci.
  contributor:
    fullname: Biradar
– volume: 62
  start-page: 161
  year: 1992
  ident: WOS:000260944900029.23
  publication-title: P NATL ACAD SCI IN A
  contributor:
    fullname: HIREMATH SP
– volume: 45
  start-page: 3257
  year: 2004
  ident: WOS:000220680400020
  article-title: Efficient one-pot preparation of 5-substituted-2-amino-1,3,4-oxadiazoles using resin-bound reagents
  publication-title: TETRAHEDRON LETTERS
  doi: 10.1016/j.tetlet.2004.02.119
  contributor:
    fullname: Coppo, FT
– volume: 60
  start-page: 175
  year: 2005
  ident: WOS:000227746500003
  article-title: Synthesis of some new 2-(2-fluoro-4-biphenylyl)propionic acid derivatives as potential anti-inflammatory agents
  publication-title: PHARMAZIE
  contributor:
    fullname: Amir, M
– volume: 30
  start-page: 179
  year: 1983
  ident: WOS:000260944900029.19
  publication-title: B INFORM I LEKOW
  contributor:
    fullname: GUMIEN D
– volume: 22
  start-page: 815
  year: 1983
  ident: WOS:A1983RM93100028
  article-title: SYNTHESIS OF CONDENSED PYRIMIDINE-DERIVATIVES FROM HETEROCYCLIC AMINES AND 1,3-DICARBONYL COMPOUNDS
  publication-title: INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY
  contributor:
    fullname: DEHURI, SN
– volume: 61
  start-page: 74
  year: 1984
  ident: WOS:A1984SS88800017
  article-title: SYNTHESIS OF SUBSTITUTED OXADIAZOLES, THIADIAZOLES AND TRIAZOLES AND EVALUATION OF THEIR BIOLOGICAL-ACTIVITY
  publication-title: JOURNAL OF THE INDIAN CHEMICAL SOCIETY
  contributor:
    fullname: HIREMATH, SP
– volume: 46
  start-page: 343
  year: 1989
  ident: MEDLINE:2517572
  article-title: [Selenazoles. XII. (1) Reaction of 4-(p-tolyl)-selenosemi-carbazides of acetic, benzoic, isonicotinic, nicotinic and picolinic acid with omega-acetophenone].
  publication-title: Acta poloniae pharmaceutica
  contributor:
    fullname: Biliski, S
– volume: 60
  start-page: 475
  year: 1983
  ident: WOS:A1983RH79500018
  article-title: STUDIES ON HETEROCYCLIC-COMPOUNDS .6. SYNTHESIS OF BRIDGEHEAD NITROGEN TRIAZINE AND PYRIMIDINE HETEROCYCLES
  publication-title: JOURNAL OF THE INDIAN CHEMICAL SOCIETY
  contributor:
    fullname: DEHURI, SN
– volume: 19
  start-page: 199
  year: 1971
  ident: WOS:000260944900029.31
  publication-title: FARM BUCHUREST
  contributor:
    fullname: SIMITI I
– volume: 16
  start-page: 2559
  year: 2006
  ident: WOS:000236564500052
  article-title: Hetaryl imidazoles: Novel dual inhibitors of VEGF receptors I and II (vol 16, pg 1440, 2006)
  publication-title: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
  doi: 10.1016/j.bmcl.2006.01.119
  contributor:
    fullname: Kiselyov, AS
– volume: 13
  start-page: 804
  year: 1975
  ident: WOS:A1975AP52800013
  article-title: BENZOTHIAZOLE DERIVATIVES .5. SYNTHESIS OF SOME 2-(5'-SUBSTITUTED AMINO-1',3',4'-OXADIAZOL-2'-YL)-BENZOTHIAZOLES, 2-(5'-SUBSTITUTED AMINO-1',3',4'-THIADIAZOL-2'-YL)-BENZOTHIAZOLES AND 2-(3'-MERCAPTO-4'-SUBSTITUTED 4'H-1',2',4'-TRIAZOL-5'-YL)-BENZOTHIAZOLES AS POTENTIAL ANTI-INFLAMMATORY AGENTS
  publication-title: INDIAN JOURNAL OF CHEMISTRY
  contributor:
    fullname: SAWHNEY, SN
– start-page: 1271
  year: 1984
  ident: WOS:000260944900029.24
  publication-title: KHIM GETEROTSIKL+
  contributor:
    fullname: KELZUEV VI
– volume: 311
  start-page: 539
  year: 1969
  ident: WOS:A1969E332900002
  article-title: 2-AMINO-1,3,4-OXADIAZOLES .28. SYNTHESIS AND REACTIONS OF 4-AMINO-5-ARYLAMINO-SYM.-TRIAZOLES
  publication-title: JOURNAL FUR PRAKTISCHE CHEMIE
  contributor:
    fullname: GEHLEN, H
– volume: 61
  start-page: 5323
  year: 2005
  ident: WOS:000229484400016
  article-title: The rapid preparation of 2-aminosulfonamide-1,3,4-oxadiazoles using polymer-supported reagents and microwave heating
  publication-title: TETRAHEDRON
  doi: 10.1016/j.tet.2005.03.062
  contributor:
    fullname: Baxendale, IR
– volume: 71
  start-page: 9548
  year: 2006
  ident: WOS:000242426900046
  article-title: Superior reactivity of thiosemicarbazides in the synthesis of 2-amino-1,3,4-oxadiazoles
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
  doi: 10.1021/jo0618730
  contributor:
    fullname: Dolman, SJ
– volume: 7
  start-page: 760
  year: 1969
  ident: WOS:A1969E050000007
  article-title: 1,3,4-OXA(THIA)DIAZOLES .4. NUCLEOPHILIC DISPLACEMENTS ON SOME 2-SUBSTITUTED-5-ARYL-(ARALKYL)-1,3,4-OXADIAZOLES
  publication-title: INDIAN JOURNAL OF CHEMISTRY
  contributor:
    fullname: MADHAVAN, R
– volume: 31
  start-page: 819
  year: 1996
  ident: WOS:A1996VM47400009
  article-title: Design, synthesis and antiinflammatory activity of some 1,3,4-oxadiazole derivatives
  publication-title: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
  contributor:
    fullname: Omar, FA
– year: 2006
  ident: WOS:000260944900029.7
– start-page: 382
  year: 2001
  ident: WOS:000167476000017
  article-title: Synthesis of 1,3,4-oxadiazoles using polymer-supported reagents
  publication-title: SYNLETT
  contributor:
    fullname: Brain, CT
– year: 2006
  ident: WOS:000260944900029.1
– year: 2005
  ident: WOS:000260944900029.3
– volume: 16
  start-page: 12
  year: 2005
  ident: WOS:000226267600003
  article-title: New access to pyrazole, oxa(thia)diazole and oxadiazine derivatives
  publication-title: HETEROATOM CHEMISTRY
  contributor:
    fullname: Hassan, AA
– year: 2004
  ident: WOS:000260944900029.5
– volume: 62
  start-page: 3309
  year: 2006
  ident: WOS:000236486100013
  article-title: Synthesis and ring transformations of 1-amino-1,2,3,9a-tetrahydroimidazo[ 1,2-a]indol-2(9H)-ones
  publication-title: TETRAHEDRON
  doi: 10.1016/j.tet.2006.01.054
  contributor:
    fullname: Dumciute, J
– volume: 37
  start-page: 159
  year: 1980
  ident: WOS:A1980KC89600004
  article-title: SELENAZOLES .8. REACTIONS OF 4-R-SELENOSEMICARBAZIDES OF ACETIC, BENZOIC, NICOTINIC AND PICOLINIC-ACID WITH CHLOROACETONE
  publication-title: ACTA POLONIAE PHARMACEUTICA
  contributor:
    fullname: MARCEWICZROJEWSKA, B
– volume: 45
  start-page: 123
  year: 2007
  ident: WOS:000243695200004
  article-title: N-15 NMR study of substituted 2-(phenylamino)-5-phenyl-1,3,4-oxadiazoles
  publication-title: MAGNETIC RESONANCE IN CHEMISTRY
  doi: 10.1002/mrc.1928
  contributor:
    fullname: Gierczyk, B
– year: 2003
  ident: WOS:000260944900029.20
  publication-title: 226 ACS NAT M
  contributor:
    fullname: HANDLON AL
– year: 2006
  ident: WOS:000260944900029.2
– volume: 16
  start-page: 1191
  year: 2006
  ident: WOS:000235284700019
  article-title: Oxadiazole derivatives as a novel class of antimitotic agents: Synthesis, inhibition of tubulin polymerization, and activity in tumor cell lines
  publication-title: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
  doi: 10.1016/j.bmcl.2005.11.094
  contributor:
    fullname: Ouyang, XH
– year: 2005
  ident: WOS:000260944900029.4
– year: 2004
  ident: WOS:000260944900029.6
– start-page: 382
  year: 2001
  ident: 10.1016/j.tetlet.2008.09.057_bib21
  publication-title: Synlett
  doi: 10.1055/s-2001-11404
  contributor:
    fullname: Brain
– volume: 61
  start-page: 74
  year: 1984
  ident: 10.1016/j.tetlet.2008.09.057_bib3_2
  publication-title: J. Indian Chem. Soc.
  contributor:
    fullname: Hiremath
– volume: 45
  start-page: 123
  year: 2007
  ident: 10.1016/j.tetlet.2008.09.057_bib17
  publication-title: Magn. Reson. Chem.
  doi: 10.1002/mrc.1928
  contributor:
    fullname: Gierczyk
– volume: 45
  start-page: 3257
  year: 2004
  ident: 10.1016/j.tetlet.2008.09.057_bib15
  publication-title: Tetrahedron Lett.
  doi: 10.1016/j.tetlet.2004.02.119
  contributor:
    fullname: Coppo
– volume: 16
  start-page: 1191
  year: 2006
  ident: 10.1016/j.tetlet.2008.09.057_bib3a
  publication-title: Bioorg. Med. Chem. Lett.
  doi: 10.1016/j.bmcl.2005.11.094
  contributor:
    fullname: Ouyang
– volume: 61
  start-page: 5323
  year: 2005
  ident: 10.1016/j.tetlet.2008.09.057_bib19
  publication-title: Tetrahedron
  doi: 10.1016/j.tet.2005.03.062
  contributor:
    fullname: Baxendale
– volume: 31
  start-page: 819
  year: 1996
  ident: 10.1016/j.tetlet.2008.09.057_bib7
  publication-title: Eur. J. Med. Chem.
  doi: 10.1016/0223-5234(96)83976-6
  contributor:
    fullname: Omar
– ident: 10.1016/j.tetlet.2008.09.057_bib1_2
– start-page: 1271
  year: 1984
  ident: 10.1016/j.tetlet.2008.09.057_bib12
  publication-title: Khim. Geterotsikl.
  contributor:
    fullname: Kelarev
– volume: 25
  start-page: 9548
  year: 2006
  ident: 10.1016/j.tetlet.2008.09.057_bib4_3
  publication-title: J. Org. Chem.
  doi: 10.1021/jo0618730
  contributor:
    fullname: Dolman
– ident: 10.1016/j.tetlet.2008.09.057_bib1_4
– volume: 22B
  start-page: 815
  year: 1983
  ident: 10.1016/j.tetlet.2008.09.057_bib13
  publication-title: Indian J. Chem. Sect. B: Org. Chem. Including Med. Chem.
  contributor:
    fullname: Dehuri
– ident: 10.1016/j.tetlet.2008.09.057_bib1e
– volume: 7
  start-page: 760
  year: 1969
  ident: 10.1016/j.tetlet.2008.09.057_bib1_6
  publication-title: Indian J. Chem.
  contributor:
    fullname: Madhavan
– volume: 16
  start-page: 2559
  year: 2006
  ident: 10.1016/j.tetlet.2008.09.057_bib2b
  publication-title: Bioorg. Med. Chem. Lett.
  doi: 10.1016/j.bmcl.2006.01.119
  contributor:
    fullname: Kiselyov
– volume: 13
  start-page: 804
  year: 1975
  ident: 10.1016/j.tetlet.2008.09.057_bib10
  publication-title: Indian J. Chem.
  contributor:
    fullname: Sawhney
– ident: 10.1016/j.tetlet.2008.09.057_bib2_1
– volume: 37
  start-page: 159
  year: 1980
  ident: 10.1016/j.tetlet.2008.09.057_bib8
  publication-title: Acta Pol. Pharm.
  contributor:
    fullname: Marcewicz-Rojewska
– volume: 46
  start-page: 343
  year: 1989
  ident: 10.1016/j.tetlet.2008.09.057_bib16
  publication-title: Acta Pol. Pharm.
  contributor:
    fullname: Bilinski
– volume: 311
  start-page: 539
  year: 1969
  ident: 10.1016/j.tetlet.2008.09.057_bib20
  publication-title: J. Prakt. Chem. (Leipzig)
  doi: 10.1002/prac.19693110403
  contributor:
    fullname: Gehlen
– volume: 62
  start-page: 161
  year: 1992
  ident: 10.1016/j.tetlet.2008.09.057_bib11
  publication-title: Proc. Natl. Acad. Sci., India Sec. A: Phys. Sci.
  contributor:
    fullname: Hiremath
– ident: 10.1016/j.tetlet.2008.09.057_bib2c
– ident: 10.1016/j.tetlet.2008.09.057_bib1_1
– volume: 60
  start-page: 475
  year: 1983
  ident: 10.1016/j.tetlet.2008.09.057_bib14
  publication-title: J. Indian Chem. Soc.
  contributor:
    fullname: Dehuri
– ident: 10.1016/j.tetlet.2008.09.057_bib1_3
– volume: 62
  start-page: 3309
  year: 2006
  ident: 10.1016/j.tetlet.2008.09.057_bib4_1
  publication-title: Tetrahedron
  doi: 10.1016/j.tet.2006.01.054
  contributor:
    fullname: Dumciute
– volume: 30
  start-page: 179
  year: 1983
  ident: 10.1016/j.tetlet.2008.09.057_bib9
  publication-title: Biuletyn Informacyjny Instytutu Lekow
  contributor:
    fullname: Gumien
– ident: 10.1016/j.tetlet.2008.09.057_bib2_4
– volume: 60
  start-page: 175
  year: 2005
  ident: 10.1016/j.tetlet.2008.09.057_bib4_2
  publication-title: Pharmazie
  contributor:
    fullname: Amir
– volume: 7
  start-page: 760
  year: 1969
  ident: 10.1016/j.tetlet.2008.09.057_bib6
  publication-title: Indian J. Chem.
  contributor:
    fullname: Madhavan
– volume: 16
  start-page: 12
  year: 2005
  ident: 10.1016/j.tetlet.2008.09.057_bib5
  publication-title: Heteroat. Chem.
  doi: 10.1002/hc.20071
  contributor:
    fullname: Hassan
– volume: 19
  start-page: 199
  year: 1971
  ident: 10.1016/j.tetlet.2008.09.057_bib18
  publication-title: Farmacia (Bucharest, Romania)
  contributor:
    fullname: Simiti
SSID ssj0000680
Score 2.159107
Snippet A convenient one-pot method for the preparation of substituted 2-amino-1,3,4-oxadiazoles is described. A convenient one-pot method for the preparation of...
A convenient one-pot method for the preparation of substituted 2-amino-1,3,4-oxadiazoles has been developed. The method is a significant improvement over...
Source Web of Science
SourceID crossref
webofscience
elsevier
SourceType Aggregation Database
Enrichment Source
Index Database
Publisher
StartPage 6709
SubjectTerms Chemistry
Chemistry, Organic
Kinase inhibitor
One-pot cyclization
Oxadiazole
Physical Sciences
Science & Technology
Title Efficient one-pot synthesis of substituted 2-amino-1,3,4-oxadiazoles
URI https://dx.doi.org/10.1016/j.tetlet.2008.09.057
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000260944900029
Volume 49
WOS 000260944900029
WOSCitedRecordID wos000260944900029
hasFullText 1
inHoldings 1
isFullTextHit
isPrint
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1LS8NAEB60PehFfGJ9lBw8uprubh57LFGpip4seAv7yEIFk2IiqAd_u7N5SIWCIrmFLBlml29mkm--ATgxXGPZYxlRmlvCQyxQFGOUWKmxCKJMSe0-Ddzdh5Mpv3kMHlcg6XphHK2yxf4G02u0bu-ct948n89mrseX44U1e-w0XwLE4T6GI8570B9f307uFwA59jvynFvQddDVNK8qwz3pSJXizHdxanmEWhKY6iB0tQkbbfbojRsDt2Aly7dhLemGtu3AxWUtCYGRxCvyjMyLyivfc0zyylnpFdYrEScacoDxKJHPs7wgo1N2yknx5lQKPpy-0y5Mry4fkglpByUQjRl_heWfcj88o0yEgmEGIGQUh1nAaKRpJLXJaCwF0ya20mijrQyMz5nOhAyYDixje9DL0ap98FQQ-1ZYapQQ3OowRgQIqLKxCX2tjB0A6ZyTzhs9jLQjij2ljTPb0ZYiRWcOIOo8mP7Y1xQh-5eVJ4sO_36bX8ugCc7duFMqBjD6y2NJq3juOv2rg38bdQjrNWHE8QCjI-hVL6_ZMWYllRrC6tnnaNievS8TveDN
link.rule.ids 315,786,790,4521,24144,27955,27956,45618,45712
linkProvider Elsevier
linkToHtml http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1LS8NAEF5KPdSL-MT6zKHHbpvubh57lNpSte2phd7CPrJQwaSYCOrB3-5sHlJBUCS3sCHLbPLNzO433yDU0UxB2mMolooZzHxIUCSlBBuhIAkiVApltwZmc3-yZPcrb9VAw7oWxtIqK-wvMb1A6-pOv7Jmf7Ne2xpfBhfk7KHVfPEAh3dsNGB5Xb2PwRYch25NnbPD6_q5guSVx7AiNaWS91zrpX72Tz-4pcIFjffRXhU7Ojfl9A5QI04OUWtYt2w7QrejQhAC_IiTJjHepLmTvSUQ4mXrzEmNkwFKlNQA7RAsntZJigdd2mU4fbUaBe9W3ekYLcejxXCCqzYJWEG8n0PyJ-1xZxBzn1Pw_1wEoR97lASKBELpmISCU6VDI7TSyghPu4yqmAuPKs9QeoKaCczqFDnSC13DDdGSc2aUH8L_7xFpQu27SmrTRrg2TrQp1TCimib2GJXGrBpb8giM2UZBbcHo26pGANi_PNnZNvjX29xCBI0zZpudEt5Gg78MG1Z657bOPz_796SuUWuymE2j6d384RztltQRuxtzgZr580t8CfFJLq-K7-8TD2jhmg
openUrl ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Efficient+one-pot+synthesis+of+substituted+2-amino-1%2C3%2C4-oxadiazoles&rft.jtitle=Tetrahedron+letters&rft.au=Chekler%2C+Eugene+L.+Piatnitski&rft.au=Elokdah%2C+Hassan+M.&rft.au=Butera%2C+John&rft.date=2008-11-17&rft.pub=Elsevier&rft.issn=0040-4039&rft.volume=49&rft.issue=47&rft.spage=6709&rft.epage=6711&rft_id=info:doi/10.1016%2Fj.tetlet.2008.09.057&rft.externalDBID=n%2Fa&rft.externalDocID=000260944900029
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0040-4039&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0040-4039&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0040-4039&client=summon