A Practical Method for Oxazole Synthesis by Cycloisomerization of Propargyl Amides
2,5-Disubstituted and 2,4,5-trisubstituted oxazol-5-yl carbonyl compounds were prepared in good yields by a mild SiO2-mediated cycloisomerization of propargyl amides.
Saved in:
Published in | Organic letters Vol. 6; no. 20; pp. 3593 - 3595 |
---|---|
Main Authors | , , |
Format | Journal Article |
Language | English |
Published |
WASHINGTON
American Chemical Society
30.09.2004
Amer Chemical Soc |
Subjects | |
Online Access | Get full text |
Cover
Loading…
Abstract | 2,5-Disubstituted and 2,4,5-trisubstituted oxazol-5-yl carbonyl compounds were prepared in good yields by a mild SiO2-mediated cycloisomerization of propargyl amides. |
---|---|
AbstractList | 2,5-Disubstituted and 2,4,5-trisubstituted oxazol-5-yl carbonyl compounds were prepared in good yields by a mild SiO2-mediated cycloisomerization of propargyl amides. [reaction: see text] 2,5-disubstituted and 2,4,5-trisubstituted oxazol-5-yl carbonyl compounds were prepared in good yields by a mild SiO2-mediated cycloisomerization of propargyl amides. |
Author | Wipf, Peter Aoyama, Yasunori Benedum, Tyler E |
Author_xml | – sequence: 1 givenname: Peter surname: Wipf fullname: Wipf, Peter – sequence: 2 givenname: Yasunori surname: Aoyama fullname: Aoyama, Yasunori – sequence: 3 givenname: Tyler E surname: Benedum fullname: Benedum, Tyler E |
BackLink | https://www.ncbi.nlm.nih.gov/pubmed/15387556$$D View this record in MEDLINE/PubMed |
BookMark | eNqNkMtKxDAUhoMo3he-gGSjIDJ6kiZNuxyKN1AUL-uSJqlG2mZMWrQ-vdEZxo0LV-fn8P2Hw7eFVjvXGYT2CJwQoOTUNcAyDjxbQZuE02QigNPVZU5hA22F8ApA4iZfRxuEJ5ngPN1E91N856XqrZINvjH9i9O4dh7ffshP1xj8MHb9iwk24GrExagaZ4Nrjbefsreuw66OfTeT_nls8LS12oQdtFbLJpjdxdxGT-dnj8Xl5Pr24qqYXk9kIkQ_YQR0mpCaK2BcUSEVIyKtJYAWPM5cg9A8U0pRVjGSEgGVpiaTWV7JmuhkGx3O7868extM6MvWBmWaRnbGDaFM0xxELlgEj-ag8i4Eb-py5m0r_VgSKL8FlkuBkd1fHB2q1uhfcmEsAtkceDeVq4OyplNmiQEApYwQGgMwWtj-R1Phhq6P1eP_VyN9MKelCuWrG3wXZf7x8Rcj3pkb |
CitedBy_id | crossref_primary_10_1021_cr300333u crossref_primary_10_1021_jo9018705 crossref_primary_10_1039_B610839C crossref_primary_10_1016_j_jorganchem_2008_09_058 crossref_primary_10_1021_jo402661b crossref_primary_10_1080_00397911_2017_1406521 crossref_primary_10_1039_b817926c crossref_primary_10_1021_acs_chemrev_7b00343 crossref_primary_10_1021_acs_joc_7b01563 crossref_primary_10_1002_chem_201100382 crossref_primary_10_1080_00397911_2021_1986843 crossref_primary_10_1039_c2ob26291f crossref_primary_10_1080_07328303_2013_816852 crossref_primary_10_1016_j_tet_2014_03_063 crossref_primary_10_1021_jo4004635 crossref_primary_10_1016_j_tetlet_2019_02_011 crossref_primary_10_1021_cr500106x crossref_primary_10_1016_j_tetlet_2010_06_130 crossref_primary_10_1016_j_tetlet_2012_02_030 crossref_primary_10_3762_bjoc_13_146 crossref_primary_10_1002_slct_202204985 crossref_primary_10_1021_cr9001098 crossref_primary_10_1002_adsc_201400496 crossref_primary_10_1016_j_tet_2008_09_074 crossref_primary_10_1016_j_tetlet_2012_11_013 crossref_primary_10_1021_acs_orglett_5b01860 crossref_primary_10_1002_ajoc_201200053 crossref_primary_10_1039_D2QO01730J crossref_primary_10_1002_chem_201002098 crossref_primary_10_1002_cssc_202100225 crossref_primary_10_1021_acs_joc_8b02334 crossref_primary_10_1039_b414826f crossref_primary_10_1021_om700891k crossref_primary_10_1021_jo301288w crossref_primary_10_1021_ja110117g crossref_primary_10_1039_C9QO01298B crossref_primary_10_1039_C3OB42030B crossref_primary_10_1016_j_tetlet_2005_06_063 crossref_primary_10_1016_j_tetlet_2014_11_061 crossref_primary_10_1002_chin_200504131 crossref_primary_10_1016_j_tetlet_2014_06_104 crossref_primary_10_1002_ejoc_200601011 crossref_primary_10_1021_jo5001719 crossref_primary_10_1038_s41428_018_0038_6 crossref_primary_10_1021_ol900455m crossref_primary_10_14723_tmrsj_42_113 crossref_primary_10_1002_chem_200600735 crossref_primary_10_1021_jo8027533 crossref_primary_10_3987_REV_10_SR_E_3 crossref_primary_10_1002_adsc_201400144 crossref_primary_10_1016_j_tetlet_2006_04_092 crossref_primary_10_1246_bcsj_20180004 crossref_primary_10_1039_c3ob41566j crossref_primary_10_1016_j_tetlet_2010_01_018 crossref_primary_10_1039_D0OB01748E crossref_primary_10_1039_c2ob25310k crossref_primary_10_5012_jkcs_2011_55_4_662 crossref_primary_10_1039_C5CC05715A crossref_primary_10_1016_j_xinn_2023_100483 crossref_primary_10_1016_j_tetlet_2006_09_157 crossref_primary_10_1039_C9MD00064J crossref_primary_10_1039_C5RA07876H crossref_primary_10_1016_j_mcat_2018_03_015 crossref_primary_10_1039_C3CC48467J crossref_primary_10_1021_acs_joc_5b00222 crossref_primary_10_1016_j_tetlet_2022_154252 crossref_primary_10_1016_j_tet_2005_09_096 crossref_primary_10_3987_COM_18_S_T_81 crossref_primary_10_1021_acs_orglett_5b02408 crossref_primary_10_1039_C6CC05138C crossref_primary_10_1016_j_tetlet_2014_05_002 crossref_primary_10_1016_j_apcata_2015_02_036 crossref_primary_10_1016_j_tet_2015_06_022 crossref_primary_10_1021_jo401330t crossref_primary_10_1039_C8RA04481C crossref_primary_10_1021_jo1025332 crossref_primary_10_1039_C2OB26377G crossref_primary_10_1002_adsc_201300911 crossref_primary_10_1002_ange_202319048 crossref_primary_10_1039_b808804g crossref_primary_10_1039_c0ob01089h crossref_primary_10_1021_om1006769 crossref_primary_10_1038_nprot_2012_107 crossref_primary_10_1016_j_tet_2011_12_004 crossref_primary_10_1021_acs_joc_2c01432 crossref_primary_10_1002_anie_202319048 crossref_primary_10_1002_ejoc_201300285 crossref_primary_10_1021_cr078399y crossref_primary_10_1016_j_tetlet_2009_08_076 crossref_primary_10_1016_j_tetlet_2018_05_004 crossref_primary_10_1021_jo100941f crossref_primary_10_1021_ol302031z |
Cites_doi | 10.1021/ol0157196 10.1021/jo016048s 10.1021/ol016133m 10.1021/ol025861m 10.1021/ci030340e 10.1021/jm010533y 10.1039/b304142p 10.1021/ol0487783 10.1021/tx015574b 10.1002/anie.200300626 10.1002/0471428035 10.1021/ja00106a075 10.1002/0471649295 10.1021/jo981542q 10.1016/S0040-4039(00)96884-9 10.1016/S0040-4039(99)02290-X 10.1016/S0040-4039(98)00231-7 10.1021/cr00038a013 10.1002/jhet.5570260201 10.1002/anie.200390363 10.1021/jo00953a028 10.1016/S0040-4039(00)87585-1 10.1021/jo00066a004 10.1021/jo980505w 10.1021/ol005777b 10.1021/jo00296a059 10.1021/jo00288a077 10.1016/S0040-4039(00)91572-7 |
ContentType | Journal Article |
Copyright | Copyright © 2004 American Chemical Society |
Copyright_xml | – notice: Copyright © 2004 American Chemical Society |
DBID | 1KM 1KN BLEPL DTL FYDSC CGR CUY CVF ECM EIF NPM AAYXX CITATION 7X8 |
DOI | 10.1021/ol0485058 |
DatabaseName | Index Chemicus Current Chemical Reactions Web of Science Core Collection Science Citation Index Expanded Web of Science - Science Citation Index Expanded - 2004 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 MEDLINE Web of Science |
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 | 1523-7052 |
EndPage | 3595 |
ExternalDocumentID | 10_1021_ol0485058 15387556 000224112000042 b515478773 |
Genre | Research Support, U.S. Gov't, P.H.S Research Support, Non-U.S. Gov't Journal Article Research Support, N.I.H., Extramural |
GrantInformation_xml | – fundername: NIGMS NIH HHS; United States Department of Health & Human Services; National Institutes of Health (NIH) - USA; NIH National Institute of General Medical Sciences (NIGMS) grantid: GM-55433 – fundername: NIGMS NIH HHS grantid: GM-55433 |
GroupedDBID | - .K2 123 53G 55A 5VS 7~N AABXI ABFLS ABMVS ABPTK ABUCX ACGFS ACS AEESW AENEX AETEA AFEFF ALMA_UNASSIGNED_HOLDINGS AQSVZ BAANH CS3 DU5 DZ EBS ED ED~ F5P GNL IH9 IHE JG JG~ K2 LG6 P2P RNS ROL TN5 UI2 UNC VF5 VG9 W1F X YNT --- -DZ -~X 1KM 1KN AAHBH ABJNI ABQRX ADHLV AHGAQ BLEPL CUPRZ DTL GGK GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED CGR CUY CVF ECM EIF NPM AAYXX CITATION 7X8 |
ID | FETCH-LOGICAL-a377t-410d631f5c045c27ac4176fa00d756fa9d07d58ccc24b416170bd2e8a89baf1d3 |
IEDL.DBID | ACS |
ISICitedReferencesCount | 111 |
ISICitedReferencesURI | https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000224112000042 |
ISSN | 1523-7060 |
IngestDate | Fri Aug 16 09:13:20 EDT 2024 Thu Sep 26 16:15:12 EDT 2024 Sat Sep 28 07:48:14 EDT 2024 Tue Sep 17 23:04:01 EDT 2024 Fri Oct 11 20:11:53 EDT 2024 Thu Aug 27 13:42:08 EDT 2020 |
IsPeerReviewed | true |
IsScholarly | true |
Issue | 20 |
Keywords | FURANS MECHANISM PRODUCT ISOMERIZATION DIAZONAMIDE ALKYNYL ALLYLIC ALCOHOLS ENANTIOMER |
Language | English |
LinkModel | DirectLink |
LogoURL | https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg |
MergedId | FETCHMERGED-LOGICAL-a377t-410d631f5c045c27ac4176fa00d756fa9d07d58ccc24b416170bd2e8a89baf1d3 |
Notes | Medline ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
PMID | 15387556 |
PQID | 66907974 |
PQPubID | 23479 |
PageCount | 3 |
ParticipantIDs | webofscience_primary_000224112000042CitationCount acs_journals_10_1021_ol0485058 proquest_miscellaneous_66907974 crossref_primary_10_1021_ol0485058 webofscience_primary_000224112000042 pubmed_primary_15387556 |
ProviderPackageCode | JG~ 55A AABXI GNL VF5 7~N VG9 W1F ACS AEESW AFEFF .K2 ABMVS ABUCX IH9 BAANH AQSVZ ED~ UI2 |
PublicationCentury | 2000 |
PublicationDate | 2004-09-30 |
PublicationDateYYYYMMDD | 2004-09-30 |
PublicationDate_xml | – month: 09 year: 2004 text: 2004-09-30 day: 30 |
PublicationDecade | 2000 |
PublicationPlace | WASHINGTON |
PublicationPlace_xml | – name: WASHINGTON – name: United States |
PublicationTitle | Organic letters |
PublicationTitleAbbrev | ORG LETT |
PublicationTitleAlternate | Org. Lett |
PublicationYear | 2004 |
Publisher | American Chemical Society Amer Chemical Soc |
Publisher_xml | – name: American Chemical Society – name: Amer Chemical Soc |
References | Wipf, P (WOS:000223296800044) 2004; 6 WASSERMAN, HH (WOS:A1973Q070400028) 1973; 38 WIPF, P (WOS:A1995RY99500014) 1995; 95 Burke, MD (WOS:000187736300005) 2004; 43 Wipf, P (WOS:000072824900001) 1998; 39 WIPF, P (WOS:A1992HE90400015) 1992; 33 Marshall, JA (WOS:000082119100026) 1999; 76 Marshall, JA (WOS:000172489500015) 2001; 66 Arcadi, A (WOS:000170392300021) 2001; 3 Phillips, AJ (WOS:000086577600040) 2000; 2 Jin, Z (WOS:000187495000004) 2003; 20 MARSHALL, JA (WOS:A1995RU76100039) 1995; 60 Murcia-Soler, M (WOS:000221608000030) 2004; 44 McGovern, SL (WOS:000174844600019) 2002; 45 Wipf, P (WOS:000175585000039) 2002; 4 PALMER DC (WOS:000224112000042.17) 2004; 60 Wipf, P (WOS:000168395400004) 2001; 3 Dalvie, DK (WOS:000174679000001) 2002; 15 WIPF, P (WOS:A1993LU65500004) 1993; 58 DOW, RL (WOS:A1990CH55800077) 1990; 55 CORRIU, RJP (WOS:A1990DB31800059) 1990; 55 Coqueron, PY (WOS:000182095700021) 2003; 42 Marshall, JA (WOS:000085617000010) 2000; 41 PALE, P (WOS:A1987L570500011) 1987; 28 PALMER DC (WOS:000224112000042.16) 2003; 60 WIPF, P (WOS:A1995QC06100075) 1995; 117 NILSSON, BM (WOS:A1989U210500001) 1989; 26 Wipf P. (ol0485058b00005/ol0485058b00005_2) 1993; 58 (ol0485058b00010/ol0485058b00010_1) 2000; 41 Palmer D. C. (ol0485058b00001/ol0485058b00001_3) 2003; 60 Wipf P. (ol0485058b00005/ol0485058b00005_4) 1992; 33 Wipf P. (ol0485058b00005/ol0485058b00005_6) 2001; 3 Wipf P. (ol0485058b00006/ol0485058b00006_2) 1998; 63 Reck S. (ol0485058b00007/ol0485058b00007_2) 1998; 63 For (ol0485058b00009/ol0485058b00009_1) 1987; 28 Coqueron P.-Y. (ol0485058b00006/ol0485058b00006_4) 2003; 42 Corriu R. J. P. (ol0485058b00012/ol0485058b00012_2) 1990; 55 Wipf P. (ol0485058b00016/ol0485058b00016_1) 2004; 6 Arcadi A. (ol0485058b00006/ol0485058b00006_3) 2001; 3 Wipf P. (ol0485058b00005/ol0485058b00005_1) 1995; 117 Wipf P. (ol0485058b00005/ol0485058b00005_3) 1998; 39 (ol0485058b00003/ol0485058b00003_1) 2002; 15 Jin Z (ol0485058b00001/ol0485058b00001_2) 2003; 20 Palmer D. C. (ol0485058b00002/ol0485058b00002_1) 2004; 60 Nilsson B. M. (ol0485058b00006/ol0485058b00006_1) 1989; 26 Dow R. L (ol0485058b00007/ol0485058b00007_1) 1990; 55 Wipf P. (ol0485058b00008/ol0485058b00008_1) 2002; 4 Burke M. D. (ol0485058b00015/ol0485058b00015_1) 2004; 43 Wipf P (ol0485058b00001/ol0485058b00001_1) 1995; 95 Wasserman H. H. (ol0485058b00004/ol0485058b00004_1) 1973; 38 Phillips A. J. (ol0485058b00005/ol0485058b00005_5) 2000; 2 Corriu R. J. P. (ol0485058b00012/ol0485058b00012_1) 1982; 32 |
References_xml | – volume: 60 year: 2004 ident: WOS:000224112000042.17 publication-title: OXAZOLES SYNTHESIS B contributor: fullname: PALMER DC – volume: 117 start-page: 558 year: 1995 ident: WOS:A1995QC06100075 article-title: TOTAL SYNTHESIS OF THE ENANTIOMER OF THE ANTIVIRAL MARINE NATURAL PRODUCT HENNOXAZOLE-A publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: WIPF, P – volume: 3 start-page: 1261 year: 2001 ident: WOS:000168395400004 article-title: Synthetic studies toward diazonamide A. A novel approach for polyoxazole synthesis publication-title: ORGANIC LETTERS doi: 10.1021/ol0157196 contributor: fullname: Wipf, P – volume: 66 start-page: 8037 year: 2001 ident: WOS:000172489500015 article-title: Synthesis of (-)-deoxypukalide, the enantiomer of a degradation product of the furanocembranolide pukalide publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo016048s contributor: fullname: Marshall, JA – volume: 3 start-page: 2501 year: 2001 ident: WOS:000170392300021 article-title: Preparation of 2,5-disubstituted oxazoles from N-propargylamides publication-title: ORGANIC LETTERS doi: 10.1021/ol016133m contributor: fullname: Arcadi, A – volume: 38 start-page: 2407 year: 1973 ident: WOS:A1973Q070400028 article-title: MECHANISM OF ROBINSON-GABRIEL SYNTHESIS OF OXAZOLES publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: WASSERMAN, HH – volume: 4 start-page: 1787 year: 2002 ident: WOS:000175585000039 article-title: Synthesis of the C(1)-C(18) segment of lophotoxin and pukalide. Control of 2-alkenylfuran (E/Z)-configuration publication-title: ORGANIC LETTERS doi: 10.1021/ol025861m contributor: fullname: Wipf, P – volume: 41 start-page: 1347 year: 2000 ident: WOS:000085617000010 article-title: A new synthesis of 3-carboxy-2,5-disubstituted furans and their conversion to 5-vinyl derivatives publication-title: TETRAHEDRON LETTERS contributor: fullname: Marshall, JA – volume: 44 start-page: 1031 year: 2004 ident: WOS:000221608000030 article-title: Artificial neural networks and linear discriminant analysis: A valuable combination in the selection of new antibacterial compounds publication-title: JOURNAL OF CHEMICAL INFORMATION AND COMPUTER SCIENCES doi: 10.1021/ci030340e contributor: fullname: Murcia-Soler, M – volume: 45 start-page: 1712 year: 2002 ident: WOS:000174844600019 article-title: A common mechanism underlying promiscuous inhibitors from virtual and high-throughput screening publication-title: JOURNAL OF MEDICINAL CHEMISTRY doi: 10.1021/jm010533y contributor: fullname: McGovern, SL – volume: 60 year: 2003 ident: WOS:000224112000042.16 publication-title: OXAZOLES SYNTHESIS A contributor: fullname: PALMER DC – volume: 60 start-page: 5966 year: 1995 ident: WOS:A1995RU76100039 article-title: SYNTHESIS OF FURANS AND 2,5-DIHYDROFURANS BY AG(I)-CATALYZED ISOMERIZATION OF ALLENONES, ALKYNYL ALLYLIC ALCOHOLS, AND ALLENYLCARBINOLS publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: MARSHALL, JA – volume: 20 start-page: 584 year: 2003 ident: WOS:000187495000004 article-title: Muscarine, imidazole, oxazole, and thiazole alkaloids publication-title: NATURAL PRODUCT REPORTS doi: 10.1039/b304142p contributor: fullname: Jin, Z – volume: 6 start-page: 3009 year: 2004 ident: WOS:000223296800044 article-title: Diversity-oriented synthesis of azaspirocycles publication-title: ORGANIC LETTERS doi: 10.1021/ol0487783 contributor: fullname: Wipf, P – volume: 39 start-page: 2223 year: 1998 ident: WOS:000072824900001 article-title: Synthetic studies toward diazonamide A. Preparation of the benzofuranone-indolyloxazole fragment publication-title: TETRAHEDRON LETTERS contributor: fullname: Wipf, P – volume: 58 start-page: 3604 year: 1993 ident: WOS:A1993LU65500004 article-title: A NEW SYNTHESIS OF HIGHLY FUNCTIONALIZED OXAZOLES publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: WIPF, P – volume: 76 start-page: 263 year: 1999 ident: WOS:000082119100026 article-title: Isomerization of beta-alkynyl allylic alcohols to furans catalyzed by silver nitrate on silica gel: 2-pentyl-3-methyl-5-heptylfuran publication-title: ORGANIC SYNTHESES, VOL 76 - 1999 contributor: fullname: Marshall, JA – volume: 28 start-page: 6447 year: 1987 ident: WOS:A1987L570500011 article-title: SILVER ASSISTED HETEROCYCLIZATION OF ACETYLENIC-COMPOUNDS publication-title: TETRAHEDRON LETTERS contributor: fullname: PALE, P – volume: 26 start-page: 269 year: 1989 ident: WOS:A1989U210500001 article-title: BASE-CATALYZED CYCLIZATION OF N-PROPARGYLAMIDES TO OXAZOLES publication-title: JOURNAL OF HETEROCYCLIC CHEMISTRY contributor: fullname: NILSSON, BM – volume: 95 start-page: 2115 year: 1995 ident: WOS:A1995RY99500014 article-title: SYNTHETIC STUDIES OF BIOLOGICALLY-ACTIVE MARINE CYCLOPEPTIDES publication-title: CHEMICAL REVIEWS contributor: fullname: WIPF, P – volume: 42 start-page: 1411 year: 2003 ident: WOS:000182095700021 article-title: Iterative oxazole assembly via alpha-chloroglycinates: Total synthesis of (-)-muscoride A publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION contributor: fullname: Coqueron, PY – volume: 2 start-page: 1165 year: 2000 ident: WOS:000086577600040 article-title: Synthesis of functionalized oxazolines and oxazoles with DAST and deoxo-fluor publication-title: ORGANIC LETTERS contributor: fullname: Phillips, AJ – volume: 55 start-page: 2878 year: 1990 ident: WOS:A1990DB31800059 article-title: SILYLAMINES IN ORGANIC-SYNTHESIS - REACTIVITY OF N,N-BIS(SILYL) ENAMINES TOWARD ELECTROPHILES - A ROUTE TO SUBSTITUTED 2-AZA-1,3-BUTADIENES AND PYRIDINES publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: CORRIU, RJP – volume: 15 start-page: 269 year: 2002 ident: WOS:000174679000001 article-title: Biotransformation reactions of five-membered aromatic heterocyclic rings publication-title: CHEMICAL RESEARCH IN TOXICOLOGY doi: 10.1021/tx015574b contributor: fullname: Dalvie, DK – volume: 55 start-page: 386 year: 1990 ident: WOS:A1990CH55800077 article-title: AN EFFICIENT SYNTHESIS OF ETHYL 5-OXAZOLEACETATES publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: DOW, RL – volume: 33 start-page: 907 year: 1992 ident: WOS:A1992HE90400015 article-title: A SHORT, STEREOSPECIFIC SYNTHESIS OF DIHYDROOXAZOLES FROM SERINE AND THREONINE DERIVATIVES publication-title: TETRAHEDRON LETTERS contributor: fullname: WIPF, P – volume: 43 start-page: 46 year: 2004 ident: WOS:000187736300005 article-title: A planning strategy for diversity-oriented synthesis publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200300626 contributor: fullname: Burke, MD – volume: 60 volume-title: Oxazoles: Synthesis, reactions, and spectroscopy, Part A year: 2003 ident: ol0485058b00001/ol0485058b00001_3 doi: 10.1002/0471428035 contributor: fullname: Palmer D. C. – volume: 117 start-page: 558 year: 1995 ident: ol0485058b00005/ol0485058b00005_1 publication-title: J. Am. Chem. Soc doi: 10.1021/ja00106a075 contributor: fullname: Wipf P. – volume: 60 volume-title: Oxazoles: Synthesis, reactions, and spectroscopy, Part B year: 2004 ident: ol0485058b00002/ol0485058b00002_1 doi: 10.1002/0471649295 contributor: fullname: Palmer D. C. – volume: 4 start-page: 1787 year: 2002 ident: ol0485058b00008/ol0485058b00008_1 publication-title: Org. Lett doi: 10.1021/ol025861m contributor: fullname: Wipf P. – volume: 63 start-page: 7132 year: 1998 ident: ol0485058b00006/ol0485058b00006_2 publication-title: J. Org. Chem doi: 10.1021/jo981542q contributor: fullname: Wipf P. – volume: 28 start-page: 6447 year: 1987 ident: ol0485058b00009/ol0485058b00009_1 publication-title: Tetrahedron Lett doi: 10.1016/S0040-4039(00)96884-9 contributor: fullname: For – volume: 41 start-page: 1347 year: 2000 ident: ol0485058b00010/ol0485058b00010_1 publication-title: Tetrahedron Lett doi: 10.1016/S0040-4039(99)02290-X – volume: 6 start-page: 3009 year: 2004 ident: ol0485058b00016/ol0485058b00016_1 publication-title: Org. Lett doi: 10.1021/ol0487783 contributor: fullname: Wipf P. – volume: 39 start-page: 2223 year: 1998 ident: ol0485058b00005/ol0485058b00005_3 publication-title: Tetrahedron Lett doi: 10.1016/S0040-4039(98)00231-7 contributor: fullname: Wipf P. – volume: 3 start-page: 1261 year: 2001 ident: ol0485058b00005/ol0485058b00005_6 publication-title: Org. Lett doi: 10.1021/ol0157196 contributor: fullname: Wipf P. – volume: 95 start-page: 2115 year: 1995 ident: ol0485058b00001/ol0485058b00001_1 publication-title: Chem. Rev doi: 10.1021/cr00038a013 contributor: fullname: Wipf P – volume: 26 start-page: 269 year: 1989 ident: ol0485058b00006/ol0485058b00006_1 publication-title: J. Heterocycl. Chem doi: 10.1002/jhet.5570260201 contributor: fullname: Nilsson B. M. – volume: 3 start-page: 2501 year: 2001 ident: ol0485058b00006/ol0485058b00006_3 publication-title: Org. Lett doi: 10.1021/ol016133m contributor: fullname: Arcadi A. – volume: 42 start-page: 1411 year: 2003 ident: ol0485058b00006/ol0485058b00006_4 publication-title: Angew. Chem., Int. Ed doi: 10.1002/anie.200390363 contributor: fullname: Coqueron P.-Y. – volume: 38 start-page: 2407 year: 1973 ident: ol0485058b00004/ol0485058b00004_1 publication-title: J. Org. Chem doi: 10.1021/jo00953a028 contributor: fullname: Wasserman H. H. – volume: 32 start-page: 3257 year: 1982 ident: ol0485058b00012/ol0485058b00012_1 publication-title: Tetrahedron Lett doi: 10.1016/S0040-4039(00)87585-1 contributor: fullname: Corriu R. J. P. – volume: 58 start-page: 3604 year: 1993 ident: ol0485058b00005/ol0485058b00005_2 publication-title: J Org. Chem doi: 10.1021/jo00066a004 contributor: fullname: Wipf P. – volume: 63 start-page: 7680 year: 1998 ident: ol0485058b00007/ol0485058b00007_2 publication-title: J. Org. Chem doi: 10.1021/jo980505w contributor: fullname: Reck S. – volume: 2 start-page: 1165 year: 2000 ident: ol0485058b00005/ol0485058b00005_5 publication-title: Org. Lett doi: 10.1021/ol005777b contributor: fullname: Phillips A. J. – volume: 55 start-page: 2878 year: 1990 ident: ol0485058b00012/ol0485058b00012_2 publication-title: J. Org. Chem doi: 10.1021/jo00296a059 contributor: fullname: Corriu R. J. P. – volume: 20 start-page: 584 year: 2003 ident: ol0485058b00001/ol0485058b00001_2 publication-title: Nat. Prod. Rep doi: 10.1039/b304142p contributor: fullname: Jin Z – volume: 55 start-page: 386 year: 1990 ident: ol0485058b00007/ol0485058b00007_1 publication-title: J. Org. Chem doi: 10.1021/jo00288a077 contributor: fullname: Dow R. L – volume: 33 start-page: 907 year: 1992 ident: ol0485058b00005/ol0485058b00005_4 publication-title: Tetrahedron Lett doi: 10.1016/S0040-4039(00)91572-7 contributor: fullname: Wipf P. – volume: 43 start-page: 46 year: 2004 ident: ol0485058b00015/ol0485058b00015_1 publication-title: Angew. Chem., Int. Ed doi: 10.1002/anie.200300626 contributor: fullname: Burke M. D. – volume: 15 start-page: 269 year: 2002 ident: ol0485058b00003/ol0485058b00003_1 publication-title: Chem. Res. Toxicol doi: 10.1021/tx015574b |
SSID | ssj0011529 |
Score | 2.212405 |
Snippet | 2,5-Disubstituted and 2,4,5-trisubstituted oxazol-5-yl carbonyl compounds were prepared in good yields by a mild SiO2-mediated cycloisomerization of propargyl... [reaction: see text] 2,5-disubstituted and 2,4,5-trisubstituted oxazol-5-yl carbonyl compounds were prepared in good yields by a mild SiO2-mediated... |
Source | Web of Science |
SourceID | proquest crossref pubmed webofscience acs |
SourceType | Aggregation Database Index Database Enrichment Source Publisher |
StartPage | 3593 |
SubjectTerms | Amides - chemistry Catalysis Chemistry Chemistry, Organic Combinatorial Chemistry Techniques Cyclization Oxazoles - chemical synthesis Physical Sciences Science & Technology Silicon Dioxide - chemistry Stereoisomerism |
Title | A Practical Method for Oxazole Synthesis by Cycloisomerization of Propargyl Amides |
URI | http://dx.doi.org/10.1021/ol0485058 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000224112000042 https://www.ncbi.nlm.nih.gov/pubmed/15387556 https://search.proquest.com/docview/66907974 |
Volume | 6 |
WOS | 000224112000042 |
WOSCitedRecordID | wos000224112000042 |
hasFullText | 1 |
inHoldings | 1 |
isFullTextHit | |
isPrint | |
link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV1bT9swFD7i8jBetgFjC2PF2vqaEjsXp49VNlQhsUnrkPoW-RZU0SVTk0orv57jpCmglstTHmInsj8n5_t0jj8DdKlUWuhAu5plwgqUwJWx4q7wKTV-Jkyk62qLn9HwKrgYh-Mt-PZEBp_Rs2KKiwzjdLwNuwzjoVVYg2S0ShVgAOrXpqjMd60VTGsf9LCrDT2qfBx61vjkxtBTh5nzd_C93azTVJfc9OaV7Knbde_G50bwHt4uaSYZNOtiH7ZMfgBvkvZ0t0P4PSCNVRFiRC7rY6QJ8lfy67-4LaaGjBY5UsNyUhK5IMlCTYtJWdjsTrNtkxQZ9kfBPbte4Gv-TrQpP8DV-Y8_ydBdnq-ASHBeuQH1dOTTLFTI6xTjQgWUR5nwPM1DvPa1x3UYK6VYIGsh5EnNTCzivhQZ1f4R7ORFbj4B6YcMlVHEkKr7gTZC6Njj0gikm4wrKR3oIADp8vso0zr1zWi6mhoHvrbYpP8an41NjU5b1FKcLpvaELkp5mUaWZGP0siBjw2Y9w_BPzoPw8iB7kN0V_e9hsVQVqsl5gB9TbNkaaBujQOq45cG9xn2moIfW2ZyAjvVbG6-IJepZKdey3c3COsp |
link.rule.ids | 315,786,790,2782,27107,27955,27956,57091,57141 |
linkProvider | American Chemical Society |
linkToHtml | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV1LT9wwEB4VeoBLH0Db9AFWxTU0dh7OHldRV9uWh8RD4hb5FbRim6B1VmL59R072QVapHLKIbYTe5zM92nG3wDsU6m00IkONauEIyhJKHPFQxFTauJKmEz7bIvjbHyR_LxML3uZHHcWBl_C4kjWB_Hv1QXot2aKew3ddb4GL1OOXs7BoOJsFTFAPzTw2qgsDp0izFJF6GFX54GUfeyB_oGVT3og721Gr7uyRf49fZLJ9cG8lQfq7i8Jx-dN5A286kEnGXa75C28MPUWbBTLWm_bcDoknXARWowc-aLSBNEsObkVd83UkLNFjUDRTiyRC1Is1LSZ2MbFerpDnKSpsD_S79nVAh_ze6KN3YGL0ffzYhz21RbQLpy3YUIjncW0ShWiPMW4UAnlWSWiSPMUrwMdcZ3mSimWSE-LIqmZyUU-kKKiOn4H63VTmw9ABilDnpQxBO5xoo0QOo-4NALBJ-NKygB2cWXK_muxpQ-EM1quliaAr0sTlTed6sZTjfaWxitxuVygQ9Smmdsyc5QfiVIA7zub3g-C_3eeplkA-w-NvLofdZiGMs-dWAD0Oc2KXk7dyQi0H_83uT3YGJ8fHZaHP45_fYLNLhXIJaB8hvV2NjdfEOW0ctdv7z9AWfOU |
linkToPdf | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV1LT9wwEB6VrVS40AelpI_FqrgGYufh7HGVdkVfUJUicYv8Clp1SRDOSt399R072S1tkcoph9iO7bEz36cZfwY4oFJpoRMdalYJR1CSUOaKhyKm1MSVMJn22RYn2fF58vEiveiJojsLg52w2JL1QXy3q6911SsM0KNmhusNXXa-AQ9TThO3EcfF2TpqgL5o5PVRWRw6VZiVktDtqs4LKfunF_oHWt7phbzHmTyG03VffaLJj8N5Kw_V8i8Zx_sP5gls9-CTjLvV8hQemPoZbBarO9924NuYdAJGaDnyxV8uTRDVktOfYtnMDDlb1AgY7dQSuSDFQs2aqW1czKc7zEmaCusjDb-5XOBnrqba2OdwPnn_vTgO-1sX0D6ct2FCI53FtEoVoj3FuFAJ5VklokjzFJ8jHXGd5koplkhPjyKpmclFPpKiojrehUHd1GYPyChlyJcyhgA-TrQRQucRl0YgCGVcSRnAEGen7HeNLX1AnNFyPTUBvF2Zqbzu1DfuKrS_MmCJ0-UCHqI2zdyWmaP-SJgCeNHZ9Xcj-J_naZoFcHDb0Ov3UYdtKPMcigVA71Os6GXVnZxA-_J_g9uHR1_fTcrPH04-vYKtLiPI5aG8hkF7MzdvEOy0cuhX-C83c_YO |
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=A+practical+method+for+oxazole+synthesis+by+cycloisomerization+of+propargyl+amides&rft.jtitle=Organic+letters&rft.au=Wipf%2C+P&rft.au=Aoyama%2C+Y&rft.au=Benedum%2C+TE&rft.date=2004-09-30&rft.pub=Amer+Chemical+Soc&rft.issn=1523-7060&rft.eissn=1523-7052&rft.volume=6&rft.issue=20&rft.spage=3593&rft.epage=3595&rft_id=info:doi/10.1021%2Fol0485058&rft_id=info%3Apmid%2F15387556&rft.externalDBID=n%2Fa&rft.externalDocID=000224112000042 |
thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1523-7060&client=summon |
thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1523-7060&client=summon |
thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1523-7060&client=summon |