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Synthesis 2010(9): 1449-1452
DOI: 10.1055/s-0029-1218682
DOI: 10.1055/s-0029-1218682
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Preparation of Substituted Oxazoles by Ritter Reactions of α-Oxo Tosylates
Further Information
Received
20 November 2009
Publication Date:
19 February 2010 (online)
Publication History
Publication Date:
19 February 2010 (online)
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Abstract
The Lewis acid catalyzed Ritter reaction of α-oxo tosylates with nitriles forms the basis of an efficient synthesis of oxazoles. Oxazoles with various substituents can be readily prepared from inexpensive starting materials.
Key words
heterocycles - cyclizations - nitriles - carbocations - oxazoles - Ritter reaction
- 1 For a comprehensive review on the
synthesis, properties and applications of oxazoles, see:
The Chemistry of Heterocyclic Compounds
Vol.
60:
Taylor EC.Wipf P.Weissberger A. Wiley Interscience; New York: 2004. -
2a
Robinson R. J. Chem. Soc. 1909, 95: 2167 -
2b
Gabriel S. Ber. Dtsch. Chem. Ges. 1910, 43: 1283 - For a modern variant, see:
-
2c
Wipf P.Miller C. J. Org. Chem. 1993, 58: 3604 - For dehydration of β-hydroxy amides to oxazolines, followed by dehydrogenation, see:
-
2d
Gant TG.Meyers AI. Tetrahedron 1994, 50: 2297 -
2e
Phillips AJ.Uto Y.Wipf P.Reno MJ.Williams DR. Org. Lett. 2000, 2: 1165 - 3
Cornforth JW.Cornforth RH. J. Chem. Soc. 1947, 96 - For examples, see:
-
4a
Arcadi A.Cacchi S.Cascia S.Cascia L.Fabrizi G.Marinelli F. Org. Lett. 2001, 3: 2501 -
4b
Hashmi SK.Weyrauch JP.Frey W.Bats JW. Org. Lett. 2004, 6: 4391 -
4c
Lee YR.Yoon SH.Seo Y.Kim BS. Synthesis 2004, 2787 -
4d
Milton MD.Inada Y.Nishibayashi Y.Uemura S. Chem. Commun. 2004, 2712 -
4e
Black DA.Arndtsen BA. Tetrahedron 2005, 61: 11317 -
4f
Kumar MP.Liu R.-S. J. Org. Chem. 2006, 71: 4951 -
4g
Martín R.Cuenca A.Buchwald SL. Org. Lett. 2007, 9: 5521 -
4h
Lee K.Counceller CM.Stambuli JP. Org. Lett. 2009, 11: 1457 - For a review on the Ritter reaction, see:
-
5a
Krimen LI.Cota DJ. Org. React. (N. Y.) 1969, 17: 213 - For a Ritter-cyclization cascade that generates pyrroles, see:
-
5b
Yu M.Pagenkopf BL. Org. Lett. 2003, 5: 5099 - 6 For physical-organic studies of α-oxo
carbocations, see:
Creary X. J. Org. Chem. 1979, 44: 3938 - 7
Lora-Tamayo M.Madroñero R.Leiprand H. Chem. Ber. 1964, 97: 2230 - 8
Lee JC.Hong T. Tetrahedron Lett. 1997, 38: 8959 - 9
Lee JC.Song I.-G. Tetrahedron Lett. 2000, 41: 5891 - 10
Varma RS.Kumar D. J. Heterocycl. Chem. 1998, 35: 1533 - 11
Kotani E.Kobayashi S.Adachi M.Tsujioka T.Nakamura K.Tobinga S. Chem. Pharm. Bull. 1989, 37: 606 - 12
Nagayoshi K.Sato Y. Chem. Lett. 1983, 1355 - 13
Herrera A.Martínez-Alvarez R.Ramiro P.Molero D.Almy J. J. Org. Chem. 2006, 71: 3026 -
14a
Doyle MP.Buhro WE.Davidson JG.Elliot RC.Hoekstra JW.Oppenhuizen M. J. Org. Chem. 1980, 45: 3657 -
14b
Ibata T.Yamashita T.Kashiuchi M.Nakano S.Nakawa H. Bull. Chem. Soc. Jpn. 1984, 57: 2450 - 15 For a related approach involving
the SN2 reactions of α-oxo sulfonates with primary
amides, followed by dehydration, see:
Koser GF. Adv. Heterocycl. Chem. 2004, 86: 225 - 16 For an overview of reactions of
this type, see:
Levin JI.Laakso LM. The Chemistry of Heterocyclic Compounds Vol. 60:Taylor EC.Wipf P.Weissberger A. Wiley Interscience; New York: 2004. Chap. 3.