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.

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Published inOrganic letters Vol. 6; no. 20; pp. 3593 - 3595
Main Authors Wipf, Peter, Aoyama, Yasunori, Benedum, Tyler E
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 30.09.2004
Amer Chemical Soc
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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
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  surname: Aoyama
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  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
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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
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Issue 20
Keywords FURANS
MECHANISM
PRODUCT
ISOMERIZATION
DIAZONAMIDE
ALKYNYL ALLYLIC ALCOHOLS
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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
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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...
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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
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