An Efficient Synthesis of a Dual PPAR α/γ Agonist and the Formation of a Sterically Congested α-Aryloxyisobutyric Acid via a Bargellini Reaction

A practical synthesis of benzisoxazole 1 and its conversion to α-aryloxyisobutyric acid 2 using 1,1,1-trichloro-2-methyl-2-propanol (chloretone) was developed. Benzisoxazole 1 was formed in high yields by the action of either methanesulfonyl chloride/base upon intermediate oxime 8 or with thionyl ch...

Full description

Saved in:
Bibliographic Details
Published inJournal of organic chemistry Vol. 70; no. 21; pp. 8560 - 8563
Main Authors Cvetovich, Raymond J, Chung, John Y. L, Kress, Michael H, Amato, Joseph S, Matty, Louis, Weingarten, M. David, Tsay, Fuh-Rong, Li, Zhen, Zhou, George
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 14.10.2005
Amer Chemical Soc
Subjects
Online AccessGet full text

Cover

Loading…
Abstract A practical synthesis of benzisoxazole 1 and its conversion to α-aryloxyisobutyric acid 2 using 1,1,1-trichloro-2-methyl-2-propanol (chloretone) was developed. Benzisoxazole 1 was formed in high yields by the action of either methanesulfonyl chloride/base upon intermediate oxime 8 or with thionyl chloride/base, which initially forms cyclic sulfite 10. A highly reactive, short-lived intermediate derived from chloretone was detected by ReacIR and its half-life determined to be ∼5 min. Reaction conditions for the Bargellini reaction were developed that resulted in a 95% yield of 2 from the reaction of highly hindered phenol 1 with chloretone hemihydrate and powdered NaOH in acetone. Thus highly hindered α-aryloxyisobutyric acids can be made in a single step in high yield.
AbstractList A practical synthesis of benzisoxazole 1 and its conversion to α-aryloxyisobutyric acid 2 using 1,1,1-trichloro-2-methyl-2-propanol (chloretone) was developed. Benzisoxazole 1 was formed in high yields by the action of either methanesulfonyl chloride/base upon intermediate oxime 8 or with thionyl chloride/base, which initially forms cyclic sulfite 10. A highly reactive, short-lived intermediate derived from chloretone was detected by ReacIR and its half-life determined to be ∼5 min. Reaction conditions for the Bargellini reaction were developed that resulted in a 95% yield of 2 from the reaction of highly hindered phenol 1 with chloretone hemihydrate and powdered NaOH in acetone. Thus highly hindered α-aryloxyisobutyric acids can be made in a single step in high yield.
A practical synthesis of benzisoxazole 1 and its conversion to alpha-aryloxyisobutyric acid 2 using 1,1,1-trichloro-2-methyl-2-propanol (chloretone) was developed. Benzisoxazole I was formed in high yields by the action of either methanesulfonyl chloride/base upon intermediate oxime 8 or with thionyl chloride/base, which initially forms cyclic sulfite 10. A highly reactive, short-lived intermediate derived from chloretone was detected by ReacIR and its half-life determined to be similar to 5 min. Reaction conditions for the Bargellini reaction were developed that resulted in a 95% yield of 2 from the reaction of highly hindered phenol 1 with chloretone hemihydrate and powdered NaOH in acetone. Thus highly hindered alpha-aryloxyisobutyric acids can be made in a single step in high yield.
A practical synthesis of benzisoxazole 1 and its conversion to alpha-aryloxyisobutyric acid 2 using 1,1,1-trichloro-2-methyl-2-propanol (chloretone) was developed. Benzisoxazole 1 was formed in high yields by the action of either methanesulfonyl chloride/base upon intermediate oxime 8 or with thionyl chloride/base, which initially forms cyclic sulfite 10. A highly reactive, short-lived intermediate derived from chloretone was detected by ReacIR and its half-life determined to be approximately 5 min. Reaction conditions for the Bargellini reaction were developed that resulted in a 95% yield of 2 from the reaction of highly hindered phenol 1 with chloretone hemihydrate and powdered NaOH in acetone. Thus highly hindered alpha-aryloxyisobutyric acids can be made in a single step in high yield.
Author Li, Zhen
Cvetovich, Raymond J
Zhou, George
Weingarten, M. David
Chung, John Y. L
Kress, Michael H
Amato, Joseph S
Matty, Louis
Tsay, Fuh-Rong
Author_xml – sequence: 1
  givenname: Raymond J
  surname: Cvetovich
  fullname: Cvetovich, Raymond J
– sequence: 2
  givenname: John Y. L
  surname: Chung
  fullname: Chung, John Y. L
– sequence: 3
  givenname: Michael H
  surname: Kress
  fullname: Kress, Michael H
– sequence: 4
  givenname: Joseph S
  surname: Amato
  fullname: Amato, Joseph S
– sequence: 5
  givenname: Louis
  surname: Matty
  fullname: Matty, Louis
– sequence: 6
  givenname: M. David
  surname: Weingarten
  fullname: Weingarten, M. David
– sequence: 7
  givenname: Fuh-Rong
  surname: Tsay
  fullname: Tsay, Fuh-Rong
– sequence: 8
  givenname: Zhen
  surname: Li
  fullname: Li, Zhen
– sequence: 9
  givenname: George
  surname: Zhou
  fullname: Zhou, George
BackLink http://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=17184254$$DView record in Pascal Francis
https://www.ncbi.nlm.nih.gov/pubmed/16209608$$D View this record in MEDLINE/PubMed
BookMark eNqNkc9u1DAQhy1URLeFAy-AfACEVIU6dmI7x7D9A1IF2245RxPHWVyydrGT0jwHT4J4jz4TXrK0By744jl8v9HMfHtoxzqrEXqekrcpoenhlSN5LMTBIzRLc0oSXpBsB80IoTRhlLNdtBfCFYkvz_MnaDfllBScyBn6UVp83LZGGW17vBxt_0UHE7BrMeCjATq8WJQX-O7n4d0vXK6cNaHHYBscOXzi_Bp64-yEL3vtjYKuG_Hc2ZUOvW5iMin92Lnb0QRXD_0YEVwq0-AbAzH0DvxKd52xBl9oUJtuT9HjFrqgn23_ffT55Phy_j45-3T6YV6eJcCE7JOW103KJG2KDKDhnFLe1o0ADYRpJrJMQNFKkSommwziukXOGVeyEYTlRNRsH72e-l57922I41ZrE1QcBqx2Q6i45JwXjEXwzQQq70Lwuq2uvVmDH6uUVBsD1V8DEX2x7TnUa908gNuLR-DVFoAQb9V6sMqEB06kMqN5FrmDifuua9eGjR-l77FokjKaRZ2xyjYTyv-n56b_Y23uBtvHaDJFo1l9e58B_7Xigom8ulwsK5men8rzglQfI_9y4kGFuPfgbXT07yF-A2WLzCE
CODEN JOCEAH
CitedBy_id crossref_primary_10_1016_j_bmcl_2014_02_055
crossref_primary_10_1016_j_tetlet_2011_08_106
crossref_primary_10_1039_c0cc05786j
crossref_primary_10_1016_j_tetlet_2009_12_070
crossref_primary_10_1021_jm501829f
crossref_primary_10_1016_j_tetlet_2014_03_118
crossref_primary_10_1016_j_tet_2007_09_006
crossref_primary_10_1246_bcsj_20110155
crossref_primary_10_1021_ml500019s
crossref_primary_10_1080_00397911_2023_2272208
crossref_primary_10_1016_j_bmcl_2014_01_026
crossref_primary_10_3390_molecules26030558
crossref_primary_10_1021_jo061295n
crossref_primary_10_1002_jps_20659
crossref_primary_10_1134_S1070428020120246
crossref_primary_10_1039_c3cc46070c
crossref_primary_10_1016_j_bmcl_2007_05_081
Cites_doi 10.1016/S0960-894X(03)00702-9
10.1016/j.tetlet.2005.01.036
10.1055/s-2004-829171
10.1080/00397919508013850
10.1021/jf9601832
10.1016/S0960-894X(01)00596-0
10.1055/s-1982-29704
10.1039/P19730002220
10.1021/jm00131a008
10.1021/jo00163a042
10.1021/ja01183a082
10.1080/00397910008087389
10.1002/jhet.5570060302
10.1021/ja01629a077
10.1016/S0040-4039(00)02019-0
10.1139/v89-224
10.1002/jps.3030480707
ContentType Journal Article
Copyright Copyright © 2005 American Chemical Society
2006 INIST-CNRS
Copyright_xml – notice: Copyright © 2005 American Chemical Society
– notice: 2006 INIST-CNRS
DBID BSCLL
1KM
1KN
BLEPL
DTL
FZXEZ
IQODW
CGR
CUY
CVF
ECM
EIF
NPM
AAYXX
CITATION
7X8
DOI 10.1021/jo051027+
DatabaseName Istex
Index Chemicus
Current Chemical Reactions
Web of Science Core Collection
Science Citation Index Expanded
Web of Science - Science Citation Index Expanded - 2005
Pascal-Francis
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
Web of Science
MEDLINE
MEDLINE - Academic
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 1520-6904
EndPage 8563
ExternalDocumentID 10_1021_jo051027
16209608
17184254
000232405500043
ark_67375_TPS_81QG8Q90_N
a154652575
Genre Journal Article
GroupedDBID -
.K2
186
29L
4.4
53G
55A
5RE
5VS
7~N
85S
AABXI
ABFLS
ABMVS
ABPPZ
ABPTK
ABUCX
ABUFD
ACGFS
ACJ
ACNCT
ACS
ACTDY
AEESW
AENEX
AETEA
AFDAS
AFEFF
AFMIJ
AIDAL
ALMA_UNASSIGNED_HOLDINGS
ANTXH
AQSVZ
BAANH
CJ0
CS3
D0L
DU5
DZ
EBS
ED
ED~
EJD
F20
F5P
GJ
GNL
IH9
IHE
JG
JG~
K2
LG6
NHB
OHM
OHT
P2P
PZZ
ROL
RXW
TAE
TAF
TN5
UI2
UKR
UNC
UPT
UQL
VF5
VG9
VQA
W1F
WH7
X
XFK
YQJ
YZZ
ZCG
---
-DZ
-~X
.GJ
6TJ
AAHBH
AAYOK
ABJNI
ABQRX
ACBEA
ACGFO
ADHLV
AGXLV
AHGAQ
BSCLL
CUPRZ
GGK
IH2
XOL
XSW
YQT
ZCA
1KM
1KN
BLEPL
DTL
GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED
.HR
123
1WB
3EH
41~
ABFRP
ABHMW
ACBNA
AFFDN
AGHSJ
AGJRR
AI.
D0S
FDB
IQODW
MVM
RNS
T9H
UBC
UMD
VH1
X7L
XXG
YXA
YXE
YYP
ZE2
ZGI
CGR
CUY
CVF
ECM
EIF
NPM
AAYXX
ACRPL
CITATION
7X8
ID FETCH-LOGICAL-a378t-f6bd1382d94aad66226fbd7aea03e37447a9f871c38d4a96095636c8d703507b3
IEDL.DBID ACS
ISICitedReferencesCount 22
ISICitedReferencesURI https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000232405500043
ISSN 0022-3263
IngestDate Fri Oct 25 01:06:16 EDT 2024
Fri Dec 06 00:46:04 EST 2024
Sat Sep 28 08:35:29 EDT 2024
Sun Oct 29 17:09:09 EDT 2023
Fri Dec 13 18:06:06 EST 2024
Fri Nov 22 22:39:32 EST 2024
Wed Oct 30 09:21:46 EDT 2024
Thu Aug 27 13:41:56 EDT 2020
IsPeerReviewed true
IsScholarly true
Issue 21
Keywords BENZOXAZOLES
OXIMES
AGENTS
DERIVATIVES
BECKMANN REARRANGEMENT
CHLORIDE
Isobutyric acid
Agonist
Steric hindrance
Oxime
Aromatic compound
Fluorine Organic compounds
Chemical synthesis
Oxygen nitrogen heterocycle
Language English
License CC BY 4.0
LinkModel DirectLink
LogoURL https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg
MergedId FETCHMERGED-LOGICAL-a378t-f6bd1382d94aad66226fbd7aea03e37447a9f871c38d4a96095636c8d703507b3
Notes istex:4E6B8622D0503A3103C9F9C2AC934DAF5F3AA36C
ark:/67375/TPS-81QG8Q90-N
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
PMID 16209608
PQID 68666933
PQPubID 23479
PageCount 4
ParticipantIDs crossref_primary_10_1021_jo051027
webofscience_primary_000232405500043
webofscience_primary_000232405500043CitationCount
proquest_miscellaneous_68666933
pubmed_primary_16209608
pascalfrancis_primary_17184254
istex_primary_ark_67375_TPS_81QG8Q90_N
acs_journals_10_1021_jo051027
ProviderPackageCode JG~
55A
AABXI
GNL
VF5
7~N
ACJ
VG9
W1F
ANTXH
ACS
AEESW
AFEFF
.K2
ABMVS
ABUCX
IH9
BAANH
AQSVZ
ED~
UI2
PublicationCentury 2000
PublicationDate 2005-10-14
PublicationDateYYYYMMDD 2005-10-14
PublicationDate_xml – month: 10
  year: 2005
  text: 2005-10-14
  day: 14
PublicationDecade 2000
PublicationPlace WASHINGTON
PublicationPlace_xml – name: WASHINGTON
– name: Washington, DC
– name: United States
PublicationTitle Journal of organic chemistry
PublicationTitleAbbrev J ORG CHEM
PublicationTitleAlternate J. Org. Chem
PublicationYear 2005
Publisher American Chemical Society
Amer Chemical Soc
Publisher_xml – name: American Chemical Society
– name: Amer Chemical Soc
References CASINI, G (WOS:A1969D381700002) 1969; 6
WEIZMANN, C (WOS:A1948UB18700082) 1948; 70
Davis, RD (WOS:000223602300010) 2004
NAIR, AD (WOS:A1959WK61600006) 1959; 48
JOZICZ Z (WOS:000232405500043.16) 1897; 29
CLEWLEY, RG (WOS:A1989AR72900015) 1989; 67
JOZICZ Z (WOS:000232405500043.17) 1897; 68
Kuramochi, H (WOS:A1996UY27400054) 1996; 44
ELKASABY, MA (WOS:A1980KH94900012) 1980; 19
BHAWAL, BM (WOS:A1995RU90600003) 1995; 25
GALIMBERTI P (WOS:000232405500043.13) 1947; 77
ABRAHAM, DJ (WOS:A1989AX29400008) 1989; 32
BUTLER, RN (WOS:A1983QE88800011) 1983
STOKKER, G (WOS:A1983RA83300042) 1983; 48
Ceglia, SS (WOS:000227268200034) 2005; 46
HOGBERG, T (WOS:A1976CT90700005) 1976; 13
Liu, KG (WOS:000171885900015) 2001; 11
Adams, AD (WOS:000185322500013) 2003; 13
GILMAN, H (WOS:A1955WB87100076) 1955; 77
FUJITA, S (WOS:A1982MZ43800020) 1982
Synerholm, Martin E (BCI:BCI19462000001707) 1945; 14
Lai, JT (WOS:000166709300005) 2001; 42
BARGELLINI G (WOS:000232405500043.3) 1906; 36
CRABBE, P (WOS:A1973R359700037) 1973
Thakur, AJ (WOS:000087661400006) 2000; 30
Jozicz Z. (jo0510271b00005/jo0510271b00005_3) 1897; 29
Hogberg T. (jo0510271b00001/jo0510271b00001_1) 1976; 13
Nair A. D. (jo0510271b00017/jo0510271b00017_1) 1959; 48
Synerholm M. E. (jo0510271b00006/jo0510271b00006_2) 1945; 14
Fujita S. (jo0510271b00013/jo0510271b00013_1) 1982; 1
Clewley R. G. (jo0510271b00007/jo0510271b00007_4) 1989; 67
Butler R. N. (jo0510271b00016/jo0510271b00016_1) 1983
Casini G. (jo0510271b00010/jo0510271b00010_1) 1969; 6
Adams A. D. (jo0510271b00008/jo0510271b00008_1) 2003; 13
Crabbe P. (jo0510271b00011/jo0510271b00011_1) 1973
Stokker G. (jo0510271b00012/jo0510271b00012_1) 1983; 48
Gilman H. (jo0510271b00007/jo0510271b00007_1) 1955; 77
Lai J. T. (jo0510271b00007/jo0510271b00007_5) 2001; 42
Weizmann C. (jo0510271b00007/jo0510271b00007_3) 1948; 70
Thakur A. S. (jo0510271b00015/jo0510271b00015_1) 2000; 30
Galimberti P. (jo0510271b00007/jo0510271b00007_2) 1947; 77
Bargellini G. (jo0510271b00005/jo0510271b00005_1) 1906; 36
Jozicz Z. (jo0510271b00005/jo0510271b00005_2) 1897; 68
Bhawal B. M. (jo0510271b00014/jo0510271b00014_1) 1995; 25
Elkasaby M. A. (jo0510271b00010/jo0510271b00010_2) 1980; 19
Abraham D. J. (jo0510271b00002/jo0510271b00002_1) 1989; 32
Liu K. G. (jo0510271b00004/jo0510271b00004_1) 2001; 11
Davis R. D. (jo0510271b00006/jo0510271b00006_1) 2004
Ceglia S. S. (jo0510271b00009/jo0510271b00009_1) 2005; 46
Kuramochi H. (jo0510271b00003/jo0510271b00003_1) 1996; 44
References_xml – volume: 32
  start-page: 2460
  year: 1989
  ident: WOS:A1989AX29400008
  article-title: DESIGN, SYNTHESIS, AND TESTING OF POTENTIAL ANTISICKLING AGENTS .7. ETHACRYNIC-ACID ANALOGS
  publication-title: JOURNAL OF MEDICINAL CHEMISTRY
  contributor:
    fullname: ABRAHAM, DJ
– volume: 25
  start-page: 3315
  year: 1995
  ident: WOS:A1995RU90600003
  article-title: USE OF ZEOLITE CATALYSTS FOR EFFICIENT SYNTHESIS OF BENZOXAZOLES VIA BECKMANN REARRANGEMENT
  publication-title: SYNTHETIC COMMUNICATIONS
  contributor:
    fullname: BHAWAL, BM
– volume: 48
  start-page: 390
  year: 1959
  ident: WOS:A1959WK61600006
  article-title: THE KINETICS OF DEGRADATION OF CHLOROBUTANOL
  publication-title: JOURNAL OF THE AMERICAN PHARMACEUTICAL ASSOCIATION
  contributor:
    fullname: NAIR, AD
– volume: 14
  start-page: 91
  year: 1945
  ident: BCI:BCI19462000001707
  article-title: The preparation of some substituted phenoxy alkyl carb-oxylic acids and their properties as growth substances
  publication-title: CONTR BOYCE THOMPSON INST
  contributor:
    fullname: Synerholm, Martin E
– start-page: 18
  year: 1983
  ident: WOS:A1983QE88800011
  article-title: DIRECT DETECTION OF INTERMEDIATES AND SYNTHETIC APPLICATIONS OF THE REACTION OF THIONYL CHLORIDE WITH OXIMES OF SUBSTITUTED ACETOPHENONES AND BENZALDEHYDES - BECKMANN REARRANGEMENTS
  publication-title: JOURNAL OF CHEMICAL RESEARCH-S
  contributor:
    fullname: BUTLER, RN
– volume: 29
  start-page: 97
  year: 1897
  ident: WOS:000232405500043.16
  publication-title: ZH RUSS FIZ KHIM OVA
  contributor:
    fullname: JOZICZ Z
– volume: 36
  start-page: 329
  year: 1906
  ident: WOS:000232405500043.3
  publication-title: GAZZ CHIM ITAL
  contributor:
    fullname: BARGELLINI G
– volume: 13
  start-page: 3185
  year: 2003
  ident: WOS:000185322500013
  article-title: O-arylmandelic acids as highly selective human PPAR alpha/gamma agonists
  publication-title: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
  doi: 10.1016/S0960-894X(03)00702-9
  contributor:
    fullname: Adams, AD
– volume: 68
  start-page: 1013
  year: 1897
  ident: WOS:000232405500043.17
  publication-title: CHEM ZENTRALBL
  contributor:
    fullname: JOZICZ Z
– volume: 77
  start-page: 431
  year: 1947
  ident: WOS:000232405500043.13
  publication-title: GAZZ CHIM ITAL
  contributor:
    fullname: GALIMBERTI P
– volume: 77
  start-page: 6644
  year: 1955
  ident: WOS:A1955WB87100076
  article-title: SOME SUBSTITUTED ALPHA-(ARYLOXY)-ISOBUTYRIC ACIDS AND AMIDES
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  contributor:
    fullname: GILMAN, H
– volume: 44
  start-page: 1906
  year: 1996
  ident: WOS:A1996UY27400054
  article-title: Structural requirements of phenoxyalkanoic acids and related compounds for promotion of flowering in Sagittaria pygmaea Miq
  publication-title: JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
  contributor:
    fullname: Kuramochi, H
– volume: 11
  start-page: 2959
  year: 2001
  ident: WOS:000171885900015
  article-title: Identification of a series of PPAR-gamma/delta dual agonists via solid-phase parallel synthesis
  publication-title: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
  contributor:
    fullname: Liu, KG
– volume: 48
  start-page: 2613
  year: 1983
  ident: WOS:A1983RA83300042
  article-title: PREPARATION OF 1,2-BENZISOXAZOLES FROM SALICYLALDOXIMES VIA TRICHLOROACETYL ISOCYANATE
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
  contributor:
    fullname: STOKKER, G
– volume: 30
  start-page: 2105
  year: 2000
  ident: WOS:000087661400006
  article-title: Microwave induced bismuth trichloride catalysed Beckmann rearrangement of oximes
  publication-title: SYNTHETIC COMMUNICATIONS
  contributor:
    fullname: Thakur, AJ
– volume: 13
  start-page: 427
  year: 1976
  ident: WOS:A1976CT90700005
  article-title: POTENTIAL HYPOLIPIDEMIC AGENTS .15. SYNTHESIS AND PLASMA LIPID-LOWERING PROPERTIES OF DERIVATIVES OF 2-PHENOXY-2-METHYLPROPIONIC ACID
  publication-title: ACTA PHARMACEUTICA SUECICA
  contributor:
    fullname: HOGBERG, T
– volume: 67
  start-page: 1472
  year: 1989
  ident: WOS:A1989AR72900015
  article-title: IPSO NITRATION IN PARA-HALOPHENYL ETHERS
  publication-title: CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE
  contributor:
    fullname: CLEWLEY, RG
– volume: 6
  start-page: 279
  year: 1969
  ident: WOS:A1969D381700002
  article-title: ON 1,2-BENZISOXAZOLE-3-ACETIC ACID AND 3-METHYL-1,2-BENZISOXAZOLE - A RESTATEMENT
  publication-title: JOURNAL OF HETEROCYCLIC CHEMISTRY
  contributor:
    fullname: CASINI, G
– volume: 19
  start-page: 571
  year: 1980
  ident: WOS:A1980KH94900012
  article-title: SYNTHESIS OF NEW ISOXAZOLES FROM ISOXAZOLINES, CHALKONES, CHALKONE DIBROMIDES, EPOXIDES AND ACETYLATED KETOXIMES AND THEIR CONVERSION INTO NOVEL HETEROCYCLES
  publication-title: INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY
  contributor:
    fullname: ELKASABY, MA
– start-page: 68
  year: 1982
  ident: WOS:A1982MZ43800020
  article-title: THE BECKMANN REARRANGEMENT BY MEANS OF PHOSPHORYL CHLORIDE N,N-DIMETHYLACETAMIDE - A NOVEL AND CONVENIENT METHOD FOR PREPARING BENZOXAZOLES
  publication-title: SYNTHESIS-STUTTGART
  contributor:
    fullname: FUJITA, S
– volume: 42
  start-page: 557
  year: 2001
  ident: WOS:000166709300005
  article-title: Totally hindered phenols. 2,6-di-t-butyl-4-(1,1-dialkyl-1-acetamide)-phenols and their persistent phenoxy radicals
  publication-title: TETRAHEDRON LETTERS
  contributor:
    fullname: Lai, JT
– volume: 70
  start-page: 1153
  year: 1948
  ident: WOS:A1948UB18700082
  article-title: THE SYNTHESIS OF ALPHA-ALKOXYISOBUTYRIC ACIDS AND ALKYL METHACRYLATES FROM ACETONECHLOROFORM
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  contributor:
    fullname: WEIZMANN, C
– start-page: 2220
  year: 1973
  ident: WOS:A1973R359700037
  article-title: UNUSUAL BASE-INDUCED TRANSFORMATION OF 2',6'-DIHYDROXYACETOPHENONE OXIME
  publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
  contributor:
    fullname: CRABBE, P
– volume: 46
  start-page: 1731
  year: 2005
  ident: WOS:000227268200034
  article-title: A regioselective synthesis of 2,4-dialkyl resorcinols
  publication-title: TETRAHEDRON LETTERS
  doi: 10.1016/j.tetlet.2005.01.036
  contributor:
    fullname: Ceglia, SS
– start-page: 1959
  year: 2004
  ident: WOS:000223602300010
  article-title: Improved method for the synthesis of 2-methyl-2-aryloxypropanoic acid derivatives
  publication-title: SYNTHESIS-STUTTGART
  doi: 10.1055/s-2004-829171
  contributor:
    fullname: Davis, RD
– volume: 25
  start-page: 3315
  year: 1995
  ident: jo0510271b00014/jo0510271b00014_1
  publication-title: Synth. Commun.
  doi: 10.1080/00397919508013850
  contributor:
    fullname: Bhawal B. M.
– start-page: 18
  year: 1983
  ident: jo0510271b00016/jo0510271b00016_1
  publication-title: J. Chem. Res. (S)
  contributor:
    fullname: Butler R. N.
– start-page: 1959
  year: 2004
  ident: jo0510271b00006/jo0510271b00006_1
  publication-title: Synthesis
  contributor:
    fullname: Davis R. D.
– volume: 44
  start-page: 1906
  year: 1996
  ident: jo0510271b00003/jo0510271b00003_1
  publication-title: J. Agric. Food Chem.
  doi: 10.1021/jf9601832
  contributor:
    fullname: Kuramochi H.
– volume: 36
  start-page: 329
  year: 1906
  ident: jo0510271b00005/jo0510271b00005_1
  publication-title: Gazz. Chim. Ital.
  contributor:
    fullname: Bargellini G.
– volume: 13
  start-page: 427
  year: 1976
  ident: jo0510271b00001/jo0510271b00001_1
  publication-title: Acta Pharm. Suec.
  contributor:
    fullname: Hogberg T.
– volume: 14
  start-page: 91
  year: 1945
  ident: jo0510271b00006/jo0510271b00006_2
  publication-title: Contrib. Boyce Thompson Inst.
  contributor:
    fullname: Synerholm M. E.
– volume: 11
  start-page: 2959
  year: 2001
  ident: jo0510271b00004/jo0510271b00004_1
  publication-title: Bioorg. Med. Chem. Lett.
  doi: 10.1016/S0960-894X(01)00596-0
  contributor:
    fullname: Liu K. G.
– volume: 68
  start-page: 1013
  year: 1897
  ident: jo0510271b00005/jo0510271b00005_2
  publication-title: Chem. Zentralbl.
  contributor:
    fullname: Jozicz Z.
– volume: 19
  start-page: 571
  year: 1980
  ident: jo0510271b00010/jo0510271b00010_2
  publication-title: Indian J. Chem.
  contributor:
    fullname: Elkasaby M. A.
– volume: 1
  start-page: 68
  year: 1982
  ident: jo0510271b00013/jo0510271b00013_1
  publication-title: Synthesis
  doi: 10.1055/s-1982-29704
  contributor:
    fullname: Fujita S.
– start-page: 2220
  year: 1973
  ident: jo0510271b00011/jo0510271b00011_1
  publication-title: J. Chem. Soc., Perkins Trans. 1
  doi: 10.1039/P19730002220
  contributor:
    fullname: Crabbe P.
– volume: 32
  start-page: 2460
  year: 1989
  ident: jo0510271b00002/jo0510271b00002_1
  publication-title: J. Med. Chem.
  doi: 10.1021/jm00131a008
  contributor:
    fullname: Abraham D. J.
– volume: 13
  start-page: 3185
  year: 2003
  ident: jo0510271b00008/jo0510271b00008_1
  publication-title: Bioorg. Med. Chem. Lett.
  doi: 10.1016/S0960-894X(03)00702-9
  contributor:
    fullname: Adams A. D.
– volume: 48
  start-page: 2613
  year: 1983
  ident: jo0510271b00012/jo0510271b00012_1
  publication-title: J. Org. Chem.
  doi: 10.1021/jo00163a042
  contributor:
    fullname: Stokker G.
– volume: 46
  start-page: 1731
  year: 2005
  ident: jo0510271b00009/jo0510271b00009_1
  publication-title: Tetrahedron Lett.
  doi: 10.1016/j.tetlet.2005.01.036
  contributor:
    fullname: Ceglia S. S.
– volume: 70
  start-page: 1153
  year: 1948
  ident: jo0510271b00007/jo0510271b00007_3
  publication-title: J. Am. Chem. Soc.
  doi: 10.1021/ja01183a082
  contributor:
    fullname: Weizmann C.
– volume: 30
  start-page: 2105
  year: 2000
  ident: jo0510271b00015/jo0510271b00015_1
  publication-title: Synth. Commun.
  doi: 10.1080/00397910008087389
  contributor:
    fullname: Thakur A. S.
– volume: 6
  start-page: 279
  year: 1969
  ident: jo0510271b00010/jo0510271b00010_1
  publication-title: J. Heterocycl. Chem.
  doi: 10.1002/jhet.5570060302
  contributor:
    fullname: Casini G.
– volume: 77
  start-page: 6644
  year: 1955
  ident: jo0510271b00007/jo0510271b00007_1
  publication-title: J. Am. Chem. Soc.
  doi: 10.1021/ja01629a077
  contributor:
    fullname: Gilman H.
– volume: 29
  start-page: 97
  year: 1897
  ident: jo0510271b00005/jo0510271b00005_3
  publication-title: Zh. Russ. Fiz. Khim. Ova.
  contributor:
    fullname: Jozicz Z.
– volume: 42
  start-page: 557
  year: 2001
  ident: jo0510271b00007/jo0510271b00007_5
  publication-title: Tetrahedron Lett.
  doi: 10.1016/S0040-4039(00)02019-0
  contributor:
    fullname: Lai J. T.
– volume: 67
  start-page: 1472
  year: 1989
  ident: jo0510271b00007/jo0510271b00007_4
  publication-title: Can. J. Chem.
  doi: 10.1139/v89-224
  contributor:
    fullname: Clewley R. G.
– volume: 77
  start-page: 431
  year: 1947
  ident: jo0510271b00007/jo0510271b00007_2
  publication-title: Gazz. Chim. Ital.
  contributor:
    fullname: Galimberti P.
– volume: 48
  start-page: 390
  year: 1959
  ident: jo0510271b00017/jo0510271b00017_1
  publication-title: J. Am. Pharm. Assoc.
  doi: 10.1002/jps.3030480707
  contributor:
    fullname: Nair A. D.
SSID ssj0000555
Score 1.9640769
Snippet A practical synthesis of benzisoxazole 1 and its conversion to α-aryloxyisobutyric acid 2 using 1,1,1-trichloro-2-methyl-2-propanol (chloretone) was developed....
A practical synthesis of benzisoxazole 1 and its conversion to alpha-aryloxyisobutyric acid 2 using 1,1,1-trichloro-2-methyl-2-propanol (chloretone) was...
Source Web of Science
SourceID proquest
crossref
pubmed
pascalfrancis
webofscience
istex
acs
SourceType Aggregation Database
Index Database
Enrichment Source
Publisher
StartPage 8560
SubjectTerms Butyrates - chemical synthesis
Butyrates - chemistry
Chemistry
Chemistry, Organic
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Isoxazoles - chemical synthesis
Isoxazoles - chemistry
Molecular Structure
Organic chemistry
Physical Sciences
PPAR alpha - agonists
PPAR gamma - agonists
Preparations and properties
Propionates - chemical synthesis
Propionates - chemistry
Science & Technology
Title An Efficient Synthesis of a Dual PPAR α/γ Agonist and the Formation of a Sterically Congested α-Aryloxyisobutyric Acid via a Bargellini Reaction
URI http://dx.doi.org/10.1021/jo051027
https://api.istex.fr/ark:/67375/TPS-81QG8Q90-N/fulltext.pdf
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000232405500043
https://www.ncbi.nlm.nih.gov/pubmed/16209608
https://search.proquest.com/docview/68666933
Volume 70
WOS 000232405500043
WOSCitedRecordID wos000232405500043
hasFullText 1
inHoldings 1
isFullTextHit
isPrint
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV3NbtQwEB6V9gAX_n9SaDGo4oLSbmInTo4hdKmQqLbdVuotsuOkCl0l1SZBLK_BkyDeo8_E2NnstmL5OUaZieTx2PNNxv4GYEelCMIzym3d38pmLHftUOKESMwlUplSlgt9wfnToX9wyj6eeWdr8PoPFXzX2ftcab9x-S3YcDlm3Rr-xOPlbut53oIR3PVpzx50TfOtjjxpfSPybGgjftUnIUWNxsi7LharYObKiGSiz_AexP0dnu7QycVu28jd9NvvlI5_Gdh9uDsHnyTqvOUBrGXlQ7gd9z3fHsH3qCT7hlQCYxEZz0qEh3VRkyongrxvUXc0io7J1Y-9q58kOq807S4RpSIoR4b9PchOfNyYWtBkMiNxVZ6b_6qoaUfT2QRHUdSVbJsZipAoLRT5UghUeqcPpmua8IIcZ92di8dwOtw_iQ_sedsGW1AeNHbuS6WZDVXIhFC-jwAvl4qLTAwoegVjXIQ55mkpDRQThvHOp34aKK6rnFzSJ7BeVmX2DIjEhNBXmSOEk7N8IIVAvMNkho88c0VqwRZObDJfdnViKuouZjRz01rwqp_y5LJj71gh88b4wkJATC_0aTfuJSejcRI4Rx-Co3CQHFqwfcNZll_E-I5bH7PgZe89Cc6brryIMqvaOvEDzBJDSi142jnVUtd3dRIZWLBz3csW7w0hEaIuzzNFWwuc_xGL5_zumteg2fyHkZ7DnZ6P1mEvYL2ZttkWIq1Gbpul9guMjyHg
link.rule.ids 314,780,784,2765,27076,27924,27925,56738,56788
linkProvider American Chemical Society
linkToHtml http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV3NbpwwELba5JBe-v9D2ySuFPVSkSzYGPZIabbbNlltshspN2RjE9GsoFqg6vY1-iRV3yPP1LGB3aRaqTkiZiwYj5lvGPsbhPZkAiBcEd_W_a1sSlPX7guYEAG5RCISQlOuDzgfj9jwjH4-985bmhx9FgYeooSRSlPEX7ELOAdfC-0-rv_uLtr0dKtKDYOiyeqr63nekhncZaRjEbquqiNQUt6IQJvamD_0jkheglHSppvFOri5NjKZKDR40LQzMs9vNp9c7teV2E9-_kPteLsXfIjut2AUh433PEJ3VP4YbUVdD7gn6FeY40NDMgGxCU8WOcDFMitxkWKOP9SgOx6Hp_jq98HVHxxeFJqGF_NcYpDDg-5cZCM-qUxtaDZb4KjIL8x_VtC0w_liBm-TlYWoqwWI4DDJJP6ecVB6rzeqa9rwDJ-q5gzGU3Q2OJxGQ7tt42Bz4geVnTIhNdOh7FPOJWMA-FIhfa54j4CXUOrzfgp5W0ICSblhwGOEJYH0ddXTF-QZ2siLXL1AWECCyKRyOHdSmvYE54B_qFBw6SuXJxbaBtPG7TIsY1NhdyHDaW1roTfd1MffGjaPNTJvjU8sBfj8Uu9-8714Op7EgXPyMTjp9-KRhXZuOM1qRIj38CmkFtrtvCiGedOVGJ6roi5jFkDW2CfEQs8b51rpMlcnlYGF9q572_K-ISgCFOZ5pohrIec2YlHL9655DqqX_zHSLtoaTo-P4qNPoy-v0L2Oq9ahr9FGNa_VNqCwSuyY5fcX_LkqpQ
linkToPdf http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV3NbpwwEB61idT20v80tE3iSlEvFckCxrBHSrJN_7abbCLlhmwMEckKogWqbl-jT1L1PfJMHRvYTaqVmiNixsLjsWeGmfkMsC1jdMITxzPV_VYmpalt9gUuiMBYIhaxQ1OuGpy_DtnBCf106p62gaLqhcGPKHGkUifx1a6-lGmLMGDtnhdKhWzv3V1YdfGUVSVcQThenLyu687RwW3mdEhC11mVFYrLG1ZoVQn0h6qK5CUKJm1utFjmci61TtoSDR7Bt_kcdAHKxU5diZ345z_wjref5GN42DqlJGi06AncSfKncD_s7oJ7Br-CnOxrsAm0UWQ8y9FtLLOSFCnhZK9G3tEoOCJXv3ev_pDgrFBwvITnkiAdGXT9kQ35uNI5oslkRsIiP9P_W5HTDKazCc4oKwtRVzMkIUGcSfI948j0XhWsK_jwjBwlTS_GczgZ7B-HB2Z7nYPJHc-vzJQJqRAPZZ9yLhlDxy8V0uMJ7zmoLZR6vJ9i_BY7vqRcI-Exh8W-9FT20xPOGqzkRZ6sAxEYKDKZWJxbKU17gnP0g6hI8NFLbB4bsIHijdrtWEY6025jpNPK1oA33fJHlw2qxxKat1ov5gR8eqGq4Dw3Oh6NI986_OAf9nvR0IDNG4qzGBHtPh6J1ICtTpMiXDeVkeF5UtRlxHyMHvuOY8CLRsEWvMxWwaVvwPZ1jZu_10BF6I25rk7mGmDdhixscd8V3kH18j9C2oJ7o71B9OXj8PMreNBB1lr0NaxU0zrZQGesEpt6B_4Fl98tKA
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=An+Efficient+Synthesis+of+a+Dual+PPAR+%CE%B1%2F%CE%B3+Agonist+and+the+Formation+of+a+Sterically+Congested+%CE%B1-Aryloxyisobutyric+Acid+via+a+Bargellini+Reaction&rft.jtitle=Journal+of+organic+chemistry&rft.au=CVETOVICH%2C+Raymond+J.&rft.au=CHUNG%2C+John+Y.+L.&rft.au=KRESS%2C+Michael+H.&rft.au=AMATO%2C+Joseph+S.&rft.date=2005-10-14&rft.pub=American+Chemical+Society&rft.issn=0022-3263&rft.eissn=1520-6904&rft.volume=70&rft.issue=21&rft.spage=8560&rft.epage=8563&rft_id=info:doi/10.1021%2Fjo051027%2B&rft.externalDBID=n%2Fa&rft.externalDocID=ark_67375_TPS_81QG8Q90_N
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0022-3263&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0022-3263&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0022-3263&client=summon