Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2002(12): 1740-1746
DOI: 10.1055/s-2002-33648
DOI: 10.1055/s-2002-33648
PAPER
© Georg Thieme Verlag Stuttgart · New York
A Versatile and Efficient Synthesis of 2-Alkyl and 2-Aryl-6-alkyl-2,3-dihydro-1H-pyridin-4-ones
Further Information
Received
4 April 2002
Publication Date:
05 September 2002 (online)
Publication History
Publication Date:
05 September 2002 (online)
Abstract
A versatile and efficient method for the preparation of 2-alkyl and 2-aryl-6-alkyl-2,3-dihydro-1H-pyridin-4-ones is described. The sequence involved the condensation of β-amino acids and t-butyl ketoester to give enaminoesters whose intramolecular cyclisation followed by an hydrolysis step afforded the expected products.
Key words
β-amino ester - enaminoester - dihydropyridinone - ring closure - heterocycle
-
1a
Coutts RT.Scott JR. Can. J. Pharm. Sci. 1971, 6: 78 -
1b
Brown JD.Foley MA.Comins DL. J. Am. Chem. Soc. 1988, 110: 7445 ; and references therein -
1c
Comins DL.Fulp AB. Org. Lett. 1999, 1: 1941 -
1d
Stout DM.Meyers AI. Chem. Rev. 1982, 82: 223 -
1e
Sausins A.Duburs G. Heterocycles 1988, 27: 291 -
1f
Comins DL.O" Connor S. Adv. Heterocycl. Chem. 1988, 44: 199 -
1g
Yamaguchi R.Hata E.Matsuki T.Kawanisi M. J. Org. Chem. 1987, 52: 2094 -
1h
Ogawa M.Natsume M. Heterocycles 1985, 23: 831 -
1i
Natsume M.Utsunomiya I.Yamaguchi K.Sakai S. Tetrahedron 1985, 41: 2115 -
1j
Ferles M.Pliml J. Adv. Heterocycl. Chem. 1970, 12: 43 - 2
Rault S,Renault O,Guillon J,Dallemagne P,Pfeiffer B,Lestage P, andLebrun MC. inventors; EP Patent 1,050,530. -
3a
Comins DL.Brown JD. Tetrahedron Lett. 1986, 27: 4549 -
3b
Comins DL.Killpack MO. J. Am. Chem. Soc. 1992, 114: 10972 -
3c
Comins DL.Joseph SP.Goehring RR. J. Am. Chem. Soc. 1994, 116: 4719 - 4
Sugiyama N.Yamamoto M.Kashima C. Bull. Chem. Soc. Jpn. 1970, 43: 901 ; and references cited therein -
5a
Renault O.Guillon J.Dallemagne P.Rault S. Tetrahedron Lett. 2000, 41: 681 -
5b
Leflemme N.Dallemagne P.Rault S. Tetrahedron Lett. 2001, 42: 8997 - 6
Ma D.Sun H. Org. Lett. 2000, 2: 2503 -
7a
Rodionov VM.Postovskaja EA. J. Am. Chem. Soc. 1929, 51: 841 -
7b
Johnson TR.Livak JE. J. Am. Chem. Soc. 1936, 58: 299 -
7c
Seeman JI.Secor HV.Whidby JF.Bassfield RL. Tetrahedron Lett. 1978, 22: 1901 -
7d
Secor HV.Edwards WB. J. Org. Chem. 1979, 44: 3136 -
8a
Plucinska K.Liberek B. Tetrahedron 1987, 43: 3509 -
8b
Podlech J.Seebach D. Liebigs Ann. Chem. 1995, 1217 - 9
Baldwin JE.Adlington RM.O’Neil IA.Schofield C.Spivey AC.Sweeney JB. J. Chem. Soc., Chem. Commun. 1989, 1852 - 10
Katritzky AR.Zhang S.Haleem A.Hussein AHM.Fang Y. J. Org. Chem. 2001, 66: 5606 - 11
Sutherland A.Willis CL. J. Org. Chem. 1998, 63: 7764 - 12
Baraldi PG.Simoni D.Manfredini S. Synthesis 1983, 902 - 13
Becker HGO. J. Prakt. Chem. 1961, 12: 294 - 14
Guarda A.Brandi A.Sarlo F.De Goti A.Pericciuoli F. J. Org. Chem. 1988, 53: 2426