Novel cyclization of bis-Boc-guanidines: expeditive traceless synthesis of 1,3,5-oxadiazinones under microwave conditions

A novel intramolecular cyclization was discovered during the reaction of soluble polymer supported bis-Boc-guanidines with amines under microwave irradiation, leading to an oxadiazinone skeleton. The cyclized polymer conjugates have been further utilized to generate substituted 1,3,5-oxadiazinones b...

Full description

Saved in:
Bibliographic Details
Published inChemical communications (Cambridge, England) Vol. 46; no. 48; pp. 9170 - 9172
Main Authors Yellol, Gorakh S., Chung, Tsai-Wen, Sun, Chung-Ming
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 28.12.2010
Subjects
Online AccessGet full text

Cover

Loading…
Abstract A novel intramolecular cyclization was discovered during the reaction of soluble polymer supported bis-Boc-guanidines with amines under microwave irradiation, leading to an oxadiazinone skeleton. The cyclized polymer conjugates have been further utilized to generate substituted 1,3,5-oxadiazinones by a traceless synthesis.
AbstractList A novel intramolecular cyclization was discovered during the reaction of soluble polymer supported bis-Boc-guanidines with amines under microwave irradiation, leading to an oxadiazinone skeleton. The cyclized polymer conjugates have been further utilized to generate substituted 1,3,5-oxadiazinones by a traceless synthesis.
Author Yellol, Gorakh S.
Chung, Tsai-Wen
Sun, Chung-Ming
Author_xml – sequence: 1
  givenname: Gorakh S.
  surname: Yellol
  fullname: Yellol, Gorakh S.
  organization: Natl Chiao Tung Univ, Dept Appl Chem, Lab Combinatorial Drug Discovery, Hsinchu 30010, Taiwan
– sequence: 2
  givenname: Tsai-Wen
  surname: Chung
  fullname: Chung, Tsai-Wen
  organization: Natl Chiao Tung Univ, Dept Appl Chem, Lab Combinatorial Drug Discovery, Hsinchu 30010, Taiwan
– sequence: 3
  givenname: Chung-Ming
  surname: Sun
  fullname: Sun, Chung-Ming
  email: cmsun@mail.nctu.edu.tw
  organization: Natl Chiao Tung Univ, Dept Appl Chem, Lab Combinatorial Drug Discovery, Hsinchu 30010, Taiwan
BackLink https://www.ncbi.nlm.nih.gov/pubmed/21042632$$D View this record in MEDLINE/PubMed
BookMark eNqNkUtP3TAQha2Kqry66Q-osqtECfiZ2OzoFbSVEGxAYhc59qQ1yrVvMwlw-fU4XEq3nc3M4jtHx8e7ZCumCIR8YvSIUWGOHXWOCsXM3Tuyw0QlSyX17dZ8K1PWQqptsot4R_MwpT-Qbc6o5JXgO2R9me6hL9za9eHJjiHFInVFG7D8llz5a7Ix-BABTwp4XIEPY7iHYhysgx4QC1zH8TdgwFnFDsWhKtOj9cE-hTkkFlP0MBTL4Ib0YLPUpTibpIj75H1ne4SPr3uP3JyfXS9-lBdX338uTi9Kx3U1lszRqqMaOKVdfo6QvqU1tdoq6aRUGloLwI3lxpjaCyN8V5lWVFwwx4XzYo982fiuhvRnAhybZcAcv7cR0oSNZkopplidyYMNmcMiDtA1qyEs7bBuGG3mppt_TWf486vt1C7Bv6F_q82A3gAP0KYOXYDo4A3LX8G1rGup5ksuwvhS_iJNcczSr_8vFc9Ksp1r
CitedBy_id crossref_primary_10_1007_s11030_011_9350_1
crossref_primary_10_1021_acscombsci_7b00052
crossref_primary_10_1021_co200188g
crossref_primary_10_1002_asia_201000913
crossref_primary_10_1021_jo401364s
crossref_primary_10_1016_j_tetlet_2011_03_046
crossref_primary_10_1007_s11030_013_9460_z
crossref_primary_10_1016_j_tetlet_2012_05_074
crossref_primary_10_1039_c0ob01126f
crossref_primary_10_1002_asia_201100277
crossref_primary_10_1039_c1nj20153k
crossref_primary_10_1016_j_tet_2011_06_068
crossref_primary_10_1021_ol201985p
crossref_primary_10_1021_co400010y
crossref_primary_10_1007_s11030_013_9433_2
crossref_primary_10_1002_adsc_201100640
Cites_doi 10.1016/j.bmcl.2010.01.031
10.1021/ar990140h
10.1007/128_058
10.1021/ol047926m
10.1038/nchembio0705-74
10.1038/nrd1926
10.1021/ol010191q
10.1021/ol026721f
10.1021/cr0103827
10.1021/ol901857h
10.1021/ol801123x
10.2174/1389557033488042
10.1002/3527606556
10.1021/ar700238s
10.1021/ol0172020
10.1021/ol100436r
10.1021/jm901379s
10.1016/j.tetasy.2006.06.036
10.1016/S0960-894X(99)00229-2
10.1055/s-1994-25527
10.1016/S0040-4039(98)00025-2
10.1055/s-1975-23831
10.1016/S0040-4039(00)79037-X
10.1002/cber.19000330208
10.1126/science.287.5460.1964
ContentType Journal Article
DBID 1KM
1KN
BLEPL
DTL
GIGBA
CGR
CUY
CVF
ECM
EIF
NPM
AAYXX
CITATION
7X8
DOI 10.1039/c0cc03519j
DatabaseName Index Chemicus
Current Chemical Reactions
Web of Science Core Collection
Science Citation Index Expanded
Web of Science - Science Citation Index Expanded - 2010
Medline
MEDLINE
MEDLINE (Ovid)
MEDLINE
MEDLINE
PubMed
CrossRef
MEDLINE - Academic
DatabaseTitle Web of Science
MEDLINE
Medline Complete
MEDLINE with Full Text
PubMed
MEDLINE (Ovid)
CrossRef
MEDLINE - Academic
DatabaseTitleList MEDLINE - Academic
Web of Science
MEDLINE
Database_xml – sequence: 1
  dbid: NPM
  name: PubMed
  url: https://proxy.k.utb.cz/login?url=http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed
  sourceTypes: Index Database
– sequence: 2
  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 1364-548X
EndPage 9172
ExternalDocumentID 10_1039_c0cc03519j
21042632
000284774500024
Genre Journal Article
GroupedDBID ---
-DZ
-JG
-~X
0-7
0R~
186
1KM
1KN
1TJ
29B
2WC
4.4
53G
5GY
6J9
6TJ
705
70~
7~J
AAEMU
AAHBH
AAIWI
AAJAE
AAMEH
AANOJ
AAWGC
AAXHV
AAXPP
ABASK
ABDVN
ABEMK
ABJNI
ABPDG
ABRYZ
ABXOH
ACBEA
ACGFO
ACGFS
ACIWK
ACLDK
ACNCT
ADMRA
ADSRN
AEFDR
AENEX
AENGV
AESAV
AETIL
AFLYV
AFOGI
AFRDS
AFVBQ
AGEGJ
AGKEF
AGRSR
AGSTE
AHGCF
AHGXI
ALMA_UNASSIGNED_HOLDINGS
ANBJS
ANLMG
ANUXI
APEMP
ASKNT
ASPBG
AUDPV
AVWKF
AZFZN
BLAPV
BLEPL
BSQNT
C6K
CAG
COF
CS3
DTL
DU5
EBS
ECGLT
EE0
EF-
EJD
F5P
FEDTE
GGIMP
GNO
GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED
H13
HVGLF
HZ~
H~N
IDZ
IH2
J3G
J3H
J3I
L-8
M4U
N9A
O9-
P2P
R56
R7B
R7C
R7D
RAOCF
RCNCU
RIG
ROL
RPMJG
RRA
RRC
RSCEA
SJN
SKA
SKF
SKH
SLH
TN5
TWZ
UPT
VH6
VQA
WH7
X7L
XJT
CGR
CUY
CVF
ECM
EIF
NPM
0UZ
3EH
71~
9M8
AAYOK
AAYXX
ACHDF
ACMRT
AFFNX
AI.
BBWZM
CITATION
EEHRC
F20
FA8
IDY
KC5
MVM
NDZJH
OHT
RCLXC
RNS
RRXOS
UHB
VH1
WHG
ZCG
ZKB
7X8
ID FETCH-LOGICAL-c286t-1c06f08e200f35934db070a8a54c4458ebaee29a29997d393df69b36231c23cd3
ISICitedReferencesCount 17
ISICitedReferencesURI https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000284774500024
ISSN 1359-7345
IngestDate Fri Oct 25 05:04:52 EDT 2024
Fri Aug 23 00:43:02 EDT 2024
Sat Sep 28 07:57:19 EDT 2024
Tue Sep 17 23:39:10 EDT 2024
Fri Nov 08 19:43:44 EST 2024
IsPeerReviewed true
IsScholarly true
Issue 48
Keywords CHIRAL AUXILIARIES
Language English
LinkModel OpenURL
LogoURL https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg
MergedId FETCHMERGED-LOGICAL-c286t-1c06f08e200f35934db070a8a54c4458ebaee29a29997d393df69b36231c23cd3
Notes ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
PMID 21042632
PQID 815551517
PQPubID 23479
PageCount 3
ParticipantIDs webofscience_primary_000284774500024CitationCount
proquest_miscellaneous_815551517
webofscience_primary_000284774500024
pubmed_primary_21042632
crossref_primary_10_1039_c0cc03519j
PublicationCentury 2000
PublicationDate 2010-12-28
PublicationDateYYYYMMDD 2010-12-28
PublicationDate_xml – month: 12
  year: 2010
  text: 2010-12-28
  day: 28
PublicationDecade 2010
PublicationPlace CAMBRIDGE
PublicationPlace_xml – name: CAMBRIDGE
– name: England
PublicationTitle Chemical communications (Cambridge, England)
PublicationTitleAbbrev CHEM COMMUN
PublicationTitleAlternate Chem Commun (Camb)
PublicationYear 2010
Publisher Royal Soc Chemistry
Publisher_xml – name: Royal Soc Chemistry
References Smits, RA (WOS:000275711000007) 2010; 53
Porcheddu, A (WOS:000225812300032) 2004; 6
Kappe, CO (WOS:000298579000011) 2005; 52
(WOS:000284774500024.1) 1988
Miel, H (WOS:000072237800028) 1998; 39
Polshettiwar, V (WOS:000256168000005) 2008; 41
McCall, WS (WOS:000257955100022) 2008; 10
Al-Obeidi, F (WOS:000210554300006) 2003; 3
Kappe, CO (WOS:000234555300017) 2006; 5
von Braun, J (WOS:000201155100005) 1900; 33
Morgan, T (WOS:000173885800032) 2002; 4
Lai, JJ (WOS:000277531000002) 2010; 12
SUN CM (WOS:000284774500024.24) 2002
GUISADO O (WOS:000284774500024.9) 1992; 33
Ho, KC (WOS:000080757600008) 1999; 9
Guery, S (WOS:000179827900010) 2002
Bairwa, R (WOS:000274714600035) 2010; 20
Schreiber, SL (WOS:000085902800047) 2000; 287
DRAKE, B (WOS:A1994NT38300009) 1994
Tan, DS (WOS:000232648200011) 2005; 1
Musiol, HJ (WOS:000172418200011) 2001; 3
GOMPPER, R (WOS:A1975AM62000019) 1975
Suna, E (WOS:000243218100002) 2006; 266
Blaney, P (WOS:000176810300005) 2002; 102
Casper, DM (WOS:000178522700048) 2002; 4
Toy, PH (WOS:000088922200005) 2000; 33
Maiti, B (WOS:000271097100016) 2009; 11
Hoover, TR (WOS:000240359100011) 2006; 17
Drake (c0cc03519j-(cit13a)/*[position()=1]) 1994
Miel (c0cc03519j-(cit17)/*[position()=1]) 1998; 39
Toy (c0cc03519j-(cit2a)/*[position()=1]) 2000; 33
von Braun (c0cc03519j-(cit15a)/*[position()=1]) 1900; 33
Shreiber (c0cc03519j-(cit1a)/*[position()=1]) 2000; 287
Polshettiwar (c0cc03519j-(cit6c)/*[position()=1]) 2008; 41
McCall (c0cc03519j-(cit15b)/*[position()=1]) 2008; 10
Maiti (c0cc03519j-(cit6b)/*[position()=1]) 2009; 11
Casper (c0cc03519j-(cit8a)/*[position()=1]) 2002; 4
Smits (c0cc03519j-(cit7a)/*[position()=1]) 2010; 53
Guisado (c0cc03519j-(cit12a)/*[position()=1]) 1992; 33
Suna (c0cc03519j-(cit5a)/*[position()=1]) 2006; 266
Blaney (c0cc03519j-(cit3)/*[position()=1]) 2002; 102
Al-Obeidi (c0cc03519j-(cit4a)/*[position()=1]) 2003; 3
Morgan (c0cc03519j-(cit14)/*[position()=1]) 2002; 4
Musiol (c0cc03519j-(cit11)/*[position()=1]) 2001; 3
Porcheddu (c0cc03519j-(cit12b)/*[position()=1]) 2004; 6
Guery (c0cc03519j-(cit13c)/*[position()=1]) 2002; 12
Lai (c0cc03519j-(cit6a)/*[position()=1]) 2010; 12
Hoover (c0cc03519j-(cit8b)/*[position()=1]) 2006; 17
Ho (c0cc03519j-(cit7c)/*[position()=1]) 1999; 9
Bairwa (c0cc03519j-(cit7b)/*[position()=1]) 2010; 20
Kappe (c0cc03519j-(cit4b)/*[position()=1]) 2006; 5
Gompper (c0cc03519j-(cit13b)/*[position()=1]) 1975
Tan (c0cc03519j-(cit1b)/*[position()=1]) 2005; 1
References_xml – volume: 20
  start-page: 1623
  year: 2010
  ident: WOS:000274714600035
  article-title: Novel molecular hybrids of cinnamic acids and guanylhydrazones as potential antitubercular agents
  publication-title: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
  doi: 10.1016/j.bmcl.2010.01.031
  contributor:
    fullname: Bairwa, R
– volume: 33
  start-page: 1438
  year: 1900
  ident: WOS:000201155100005
  article-title: The action of bromine cyanogen on tertiary amines
  publication-title: BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT
  contributor:
    fullname: von Braun, J
– volume: 33
  start-page: 546
  year: 2000
  ident: WOS:000088922200005
  article-title: Soluble polymer-supported organic synthesis
  publication-title: ACCOUNTS OF CHEMICAL RESEARCH
  doi: 10.1021/ar990140h
  contributor:
    fullname: Toy, PH
– volume: 266
  start-page: 49
  year: 2006
  ident: WOS:000243218100002
  article-title: Microwave-assisted heterocyclic chemistry
  publication-title: MICROWAVE METHODS IN ORGANIC SYNTHESIS
  doi: 10.1007/128_058
  contributor:
    fullname: Suna, E
– volume: 6
  start-page: 4925
  year: 2004
  ident: WOS:000225812300032
  article-title: New cellulose-supported reagent: A sustainable approach to guanidines
  publication-title: ORGANIC LETTERS
  doi: 10.1021/ol047926m
  contributor:
    fullname: Porcheddu, A
– start-page: 2003
  year: 2002
  ident: WOS:000179827900010
  article-title: An expeditive method for the synthesis of arginine-based chemical libraries
  publication-title: SYNLETT
  contributor:
    fullname: Guery, S
– volume: 287
  start-page: 1964
  year: 2000
  ident: WOS:000085902800047
  article-title: Target-oriented and diversity-oriented organic synthesis in drug discovery
  publication-title: SCIENCE
  contributor:
    fullname: Schreiber, SL
– start-page: 345
  year: 2002
  ident: WOS:000284774500024.24
  publication-title: COMBINATORIAL CHEM M
  contributor:
    fullname: SUN CM
– volume: 1
  start-page: 74
  year: 2005
  ident: WOS:000232648200011
  article-title: Diversity-oriented synthesis: exploring the intersections between chemistry and biology
  publication-title: NATURE CHEMICAL BIOLOGY
  doi: 10.1038/nchembio0705-74
  contributor:
    fullname: Tan, DS
– year: 1988
  ident: WOS:000284774500024.1
– volume: 5
  start-page: 51
  year: 2006
  ident: WOS:000234555300017
  article-title: The impact of microwave synthesis on drug discovery
  publication-title: NATURE REVIEWS DRUG DISCOVERY
  doi: 10.1038/nrd1926
  contributor:
    fullname: Kappe, CO
– volume: 3
  start-page: 3859
  year: 2001
  ident: WOS:000172418200011
  article-title: N,N '-Di-tert-butoxycarbonyl-1H-benzotriazole-1-carboxamidine derivatives are highly reactive guanidinylating reagents
  publication-title: ORGANIC LETTERS
  doi: 10.1021/ol010191q
  contributor:
    fullname: Musiol, HJ
– volume: 4
  start-page: 3739
  year: 2002
  ident: WOS:000178522700048
  article-title: Toward the development of a structurally novel class of chiral auxiliaries: Diastereoselective aldol reactions of a (1R,2S)-ephedrine-based 3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-one
  publication-title: ORGANIC LETTERS
  doi: 10.1021/ol026721f
  contributor:
    fullname: Casper, DM
– volume: 102
  start-page: 2607
  year: 2002
  ident: WOS:000176810300005
  article-title: Traceless solid-phase organic synthesis
  publication-title: CHEMICAL REVIEWS
  doi: 10.1021/cr0103827
  contributor:
    fullname: Blaney, P
– volume: 33
  start-page: 6541
  year: 1992
  ident: WOS:000284774500024.9
  publication-title: TETRAHEDRON LETT
  contributor:
    fullname: GUISADO O
– volume: 39
  start-page: 1565
  year: 1998
  ident: WOS:000072237800028
  article-title: Conversion of N,N '-bis(tert-butoxycarbonyl)guanidines to N-(N '-tert-butoxycarbonylamidino)ureas
  publication-title: TETRAHEDRON LETTERS
  contributor:
    fullname: Miel, H
– volume: 11
  start-page: 4826
  year: 2009
  ident: WOS:000271097100016
  article-title: Traceless Synthesis of Hydantoin Fused Tetrahydro-beta-carboline on Ionic Liquid Support in Green Media
  publication-title: ORGANIC LETTERS
  doi: 10.1021/ol901857h
  contributor:
    fullname: Maiti, B
– volume: 10
  start-page: 3255
  year: 2008
  ident: WOS:000257955100022
  article-title: Stereoselective synthesis of acyclic amino alcohols via von Braun ring opening of chiral piperidines
  publication-title: ORGANIC LETTERS
  doi: 10.1021/ol801123x
  contributor:
    fullname: McCall, WS
– start-page: 579
  year: 1994
  ident: WOS:A1994NT38300009
  article-title: A CONVENIENT PREPARATION OF MONOSUBSTITUTED N,N'-DI(BOC)-PROTECTED GUANIDINES
  publication-title: SYNTHESIS-STUTTGART
  contributor:
    fullname: DRAKE, B
– volume: 3
  start-page: 449
  year: 2003
  ident: WOS:000210554300006
  article-title: Microwave-Assisted Solid-phase Synthesis (MASS): Parallel and Combinatorial Chemical Library Synthesis
  publication-title: MINI-REVIEWS IN MEDICINAL CHEMISTRY
  doi: 10.2174/1389557033488042
  contributor:
    fullname: Al-Obeidi, F
– volume: 52
  start-page: 1
  year: 2005
  ident: WOS:000298579000011
  article-title: Microwaves in Organic and Medicinal Chemistry
  publication-title: MICROWAVES IN ORGANIC AND MEDICINAL CHEMISTRY
  doi: 10.1002/3527606556
  contributor:
    fullname: Kappe, CO
– volume: 41
  start-page: 629
  year: 2008
  ident: WOS:000256168000005
  article-title: Microwave-assisted organic synthesis and transformations using benign reaction media
  publication-title: ACCOUNTS OF CHEMICAL RESEARCH
  doi: 10.1021/ar700238s
  contributor:
    fullname: Polshettiwar, V
– volume: 4
  start-page: 597
  year: 2002
  ident: WOS:000173885800032
  article-title: A solid-phase route to N-cyanoamides
  publication-title: ORGANIC LETTERS
  doi: 10.1021/ol0172020
  contributor:
    fullname: Morgan, T
– volume: 12
  start-page: 2174
  year: 2010
  ident: WOS:000277531000002
  article-title: Multistep Microwave-Assisted Divergent Synthesis of Indolo-Fused Pyrazino-/Diazepinoquinoxalinones on PEG Support
  publication-title: ORGANIC LETTERS
  doi: 10.1021/ol100436r
  contributor:
    fullname: Lai, JJ
– volume: 53
  start-page: 2390
  year: 2010
  ident: WOS:000275711000007
  article-title: Synthesis and QSAR of Quinazoline Sulfonamides As Highly Potent Human Histamine H-4 Receptor Inverse Agonists
  publication-title: JOURNAL OF MEDICINAL CHEMISTRY
  doi: 10.1021/jm901379s
  contributor:
    fullname: Smits, RA
– volume: 17
  start-page: 1831
  year: 2006
  ident: WOS:000240359100011
  article-title: Towards the development of oxadiazinanones as chiral auxiliaries: synthesis and application of N-3-haloacetyloxadiazinanones
  publication-title: TETRAHEDRON-ASYMMETRY
  doi: 10.1016/j.tetasy.2006.06.036
  contributor:
    fullname: Hoover, TR
– start-page: 522
  year: 1975
  ident: WOS:A1975AM62000019
  article-title: 4,6-BIS[DIALKYLAMINO]-2-OXO-2H-1,3,5-OXADIAZINE
  publication-title: SYNTHESIS-STUTTGART
  contributor:
    fullname: GOMPPER, R
– volume: 9
  start-page: 1517
  year: 1999
  ident: WOS:000080757600008
  article-title: Liquid phase parallel synthesis of guanidines
  publication-title: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
  contributor:
    fullname: Ho, KC
– volume: 41
  start-page: 629
  year: 2008
  ident: c0cc03519j-(cit6c)/*[position()=1]
  publication-title: Acc. Chem. Res.
  doi: 10.1021/ar700238s
  contributor:
    fullname: Polshettiwar
– volume: 9
  start-page: 1517
  year: 1999
  ident: c0cc03519j-(cit7c)/*[position()=1]
  publication-title: Bioorg. Med. Chem. Lett.
  doi: 10.1016/S0960-894X(99)00229-2
  contributor:
    fullname: Ho
– start-page: 579
  year: 1994
  ident: c0cc03519j-(cit13a)/*[position()=1]
  publication-title: Synthesis
  doi: 10.1055/s-1994-25527
  contributor:
    fullname: Drake
– volume: 6
  start-page: 4925
  year: 2004
  ident: c0cc03519j-(cit12b)/*[position()=1]
  publication-title: Org. Lett.
  doi: 10.1021/ol047926m
  contributor:
    fullname: Porcheddu
– volume: 5
  start-page: 51
  year: 2006
  ident: c0cc03519j-(cit4b)/*[position()=1]
  publication-title: Nat. Rev. Drug Discovery
  doi: 10.1038/nrd1926
  contributor:
    fullname: Kappe
– volume: 3
  start-page: 459
  year: 2003
  ident: c0cc03519j-(cit4a)/*[position()=1]
  publication-title: Mini-Rev. Med. Chem.
  doi: 10.2174/1389557033488042
  contributor:
    fullname: Al-Obeidi
– volume: 10
  start-page: 3255
  year: 2008
  ident: c0cc03519j-(cit15b)/*[position()=1]
  publication-title: Org. Lett.
  doi: 10.1021/ol801123x
  contributor:
    fullname: McCall
– volume: 20
  start-page: 1623
  year: 2010
  ident: c0cc03519j-(cit7b)/*[position()=1]
  publication-title: Bioorg. Med. Chem. Lett.
  doi: 10.1016/j.bmcl.2010.01.031
  contributor:
    fullname: Bairwa
– volume: 12
  start-page: 2174
  year: 2010
  ident: c0cc03519j-(cit6a)/*[position()=1]
  publication-title: Org. Lett.
  doi: 10.1021/ol100436r
  contributor:
    fullname: Lai
– volume: 39
  start-page: 1565
  year: 1998
  ident: c0cc03519j-(cit17)/*[position()=1]
  publication-title: Tetrahedron Lett.
  doi: 10.1016/S0040-4039(98)00025-2
  contributor:
    fullname: Miel
– volume: 12
  start-page: 2003
  year: 2002
  ident: c0cc03519j-(cit13c)/*[position()=1]
  publication-title: Synlett
  contributor:
    fullname: Guery
– start-page: 522
  year: 1975
  ident: c0cc03519j-(cit13b)/*[position()=1]
  publication-title: Synthesis
  doi: 10.1055/s-1975-23831
  contributor:
    fullname: Gompper
– volume: 53
  start-page: 2390
  year: 2010
  ident: c0cc03519j-(cit7a)/*[position()=1]
  publication-title: J. Med. Chem.
  doi: 10.1021/jm901379s
  contributor:
    fullname: Smits
– volume: 17
  start-page: 1831
  year: 2006
  ident: c0cc03519j-(cit8b)/*[position()=1]
  publication-title: Tetrahedron: Asymmetry
  doi: 10.1016/j.tetasy.2006.06.036
  contributor:
    fullname: Hoover
– volume: 33
  start-page: 546
  year: 2000
  ident: c0cc03519j-(cit2a)/*[position()=1]
  publication-title: Acc. Chem. Res.
  doi: 10.1021/ar990140h
  contributor:
    fullname: Toy
– volume: 266
  start-page: 49
  year: 2006
  ident: c0cc03519j-(cit5a)/*[position()=1]
  publication-title: Top. Curr. Chem.
  doi: 10.1007/128_058
  contributor:
    fullname: Suna
– volume: 11
  start-page: 4826
  year: 2009
  ident: c0cc03519j-(cit6b)/*[position()=1]
  publication-title: Org. Lett.
  doi: 10.1021/ol901857h
  contributor:
    fullname: Maiti
– volume: 4
  start-page: 3739
  year: 2002
  ident: c0cc03519j-(cit8a)/*[position()=1]
  publication-title: Org. Lett.
  doi: 10.1021/ol026721f
  contributor:
    fullname: Casper
– volume: 33
  start-page: 6541
  year: 1992
  ident: c0cc03519j-(cit12a)/*[position()=1]
  publication-title: Tetrahedron Lett.
  doi: 10.1016/S0040-4039(00)79037-X
  contributor:
    fullname: Guisado
– volume: 1
  start-page: 74
  year: 2005
  ident: c0cc03519j-(cit1b)/*[position()=1]
  publication-title: Nat. Chem. Biol.
  doi: 10.1038/nchembio0705-74
  contributor:
    fullname: Tan
– volume: 3
  start-page: 3859
  year: 2001
  ident: c0cc03519j-(cit11)/*[position()=1]
  publication-title: Org. Lett.
  doi: 10.1021/ol010191q
  contributor:
    fullname: Musiol
– volume: 102
  start-page: 2607
  year: 2002
  ident: c0cc03519j-(cit3)/*[position()=1]
  publication-title: Chem. Rev.
  doi: 10.1021/cr0103827
  contributor:
    fullname: Blaney
– volume: 4
  start-page: 597
  year: 2002
  ident: c0cc03519j-(cit14)/*[position()=1]
  publication-title: Org. Lett.
  doi: 10.1021/ol0172020
  contributor:
    fullname: Morgan
– volume: 33
  start-page: 1438
  year: 1900
  ident: c0cc03519j-(cit15a)/*[position()=1]
  publication-title: Chem. Ber.
  doi: 10.1002/cber.19000330208
  contributor:
    fullname: von Braun
– volume: 287
  start-page: 1964
  year: 2000
  ident: c0cc03519j-(cit1a)/*[position()=1]
  publication-title: Science
  doi: 10.1126/science.287.5460.1964
  contributor:
    fullname: Shreiber
SSID ssj0000158
Score 2.1474319
Snippet A novel intramolecular cyclization was discovered during the reaction of soluble polymer supported bis-Boc-guanidines with amines under microwave irradiation,...
Source Web of Science
SourceID proquest
crossref
pubmed
webofscience
SourceType Aggregation Database
Index Database
Enrichment Source
StartPage 9170
SubjectTerms Amines
Azirines - chemistry
Chemistry
Chemistry, Multidisciplinary
Cyclization
Dihydropyridines - chemistry
Guanidines - chemistry
Microwaves
Physical Sciences
Polyethylene Glycols
Science & Technology
Title Novel cyclization of bis-Boc-guanidines: expeditive traceless synthesis of 1,3,5-oxadiazinones under microwave conditions
URI http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000284774500024
https://www.ncbi.nlm.nih.gov/pubmed/21042632
https://search.proquest.com/docview/815551517
Volume 46
WOS 000284774500024
WOSCitedRecordID wos000284774500024
hasFullText 1
inHoldings 1
isFullTextHit
isPrint
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1Jc9MwFNaE9gAXhp2wjWboLVWwLXkRt5IpUxjaS9MhnDKSLJdAiTuJDU3_DH-VJ1leaHIIHOLJ2PESvc9vkd77HkJ7glMtwQ8lIYRXhPksJNKXKRFMRKmixuM2tcPHJ9HRGfs4CSe93u9O1lJZyKG63lhX8j9ShX0gV1Ml-w-SbS4KO-A7yBe2IGHYbiXjk_ynvhiolbpw1ZTG9ZOzJXmXK3JeivksNVnttvvO1SWYKZsnVCyEAmMDGm65moP_5yhJQKWNKHxCkl8ZwoLr2dzw-NtGuYvBD5O498u0KoIAOp2103w1y0FNPKC6FSd2SrcpC7N6t2oa0pmA-GKWf6o2XwDH718Hp8M258CpovFSzMjntmrttHS5AnCcHNfW101eVIkgQVff0pCTmFaMkkPt9kWMQCA16SppN09ZgbHi5nQqF-JNb6Mt8KihUlWeUma1lH9rLV69yn_DEDbpiXZhnvJpe-4ttBuAJgMVuntwOP7wqcNQZlvANv-jZsCl_E179t8-z1ogs9Hnsf7N-B666wITfFCh7D7q6fkDdHtU9wN8iFYWbbiDNpxneB1tb3GLNdxgDTdYM2f5-3T_Bs6wxRlucIZbnD1CZ-8Px6Mj4hp3EBUkUUF85UWZl2h4VzMYGMpSCZZFJCJkirEw0VJoHXABrhCPU8ppmkVcgmKgvgqoSuljtGNu_RThiKcipoHkMkyZzuJESqZhdJMoSngQsz56XQ_t9LLiZ5mui6-PcD3qUxg1syYm5jovl9ME_Glw6f24j55U0mguE_ie7WbQR3td8TTH7cw0g_DJ9BQJ4En8bX42ctT7hnKieLbV0z9Hd9p35wXaKRalfgmucCFfOTj-Ab7JtnI
link.rule.ids 315,783,787,27936,27937
linkProvider Royal Society of Chemistry
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=Novel+cyclization+of+bis-Boc-guanidines%3A+expeditive+traceless+synthesis+of+1%2C3%2C5-oxadiazinones+under+microwave+conditions&rft.jtitle=Chemical+communications+%28Cambridge%2C+England%29&rft.au=Yellol%2C+Gorakh+S.&rft.au=Chung%2C+Tsai-Wen&rft.au=Sun%2C+Chung-Ming&rft.date=2010-12-28&rft.issn=1359-7345&rft.eissn=1364-548X&rft.volume=46&rft.issue=48&rft.spage=9170&rft_id=info:doi/10.1039%2Fc0cc03519j&rft.externalDBID=n%2Fa&rft.externalDocID=10_1039_c0cc03519j
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1359-7345&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1359-7345&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1359-7345&client=summon