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 2006(3): 435-438
DOI: 10.1055/s-2006-926295
DOI: 10.1055/s-2006-926295
PAPER
© Georg Thieme Verlag Stuttgart · New York
A Convenient One-Pot Synthesis of Pyrano[3,2-c]quinolin-2,5(6H)-dione and 2H,5H-Pyrano[3,2-c]chromene-2,5-dione Derivatives
Further Information
Received
20 July 2005
Publication Date:
11 January 2006 (online)
Publication History
Publication Date:
11 January 2006 (online)
Abstract
The preparation of novel pyrano[3,2-c]quinolin-2,5(6H)-dione and 2H,5H-pyrano[3,2-c]chromene-2,5-dione derivatives starting from 4-hydroxyquinolin-2(1H)-ones and 4-hydroxy-2H-chromene-2-one with chlorocarbonyl ketenes is described. This method provides a new route to produce fused pyrano derivatives in good to excellent yields in a short experimental time.
Keywords
pyrano quinolinones - chromene derivatives - chlorocarbonyl ketenes
- 1
Macloed AM.Grimwood S.Barton C.Bristow L.Saywell K.Marshall GR.Ball G. J. Med. Chem. 1995, 38: 2239 - 2
Kappe T.Aigner R.Hohengassner P.Stadlbauer W. J. Prakt. Chem. 1994, 336: 569 - 3
Kepe V.Polanc S.Kocevar M. Heterocycles 1998, 48: 671 - 4
Cho CG.Park JS.Jung IH.Lee H. Tetrahedron Lett. 2001, 42: 1065 - 5
Kim WS.Lee JH.Kang J.Cho CG. Tetrahedron Lett. 2004, 45: 1683 - 6
Zhang X.Hinkel B.Ballantyne L.Gonzales S.Pena MR. J. Heterocycl. Chem. 1997, 34: 1061 - 7
Afarinkia K.Vinader V.Nelson TD.Posner GH. Tetrahedron 1992, 48: 9111 - 8
Lee HS.Kim D.Won H.Choi JH.Lee H.Cho CG. Tetrahedron Lett. 2002, 43: 5591 - 9
Lacey NR. J. Chem. Soc. 1954, 850 - 10
Sheibani H.Islami MR.Khabazzadeh H.Saidi K. Tetrahedron 2004, 60: 5932 - 11
Sheibani H.Bernhardt PV.Wentrup C. J. Org. Chem. 2005, 70: 5859 - 12
Potts KT.Dery MO.Kullnig R. J. Chem. Soc., Chem. Commun. 1987, 840 - 13
Miao H.Yang Z. Org. Lett. 2000, 2: 1765 - 14
Kadis S.Ciegler A.Ajl S. Microbial Toxins Vol. 7: Academic Press; New York: 1972. Chap. 1. - 15
Ellis GP.West GB. Prog. Med. Chem. 1974, 10: 109 - 16
Wells P.Morrison H. J. Am. Chem. Soc. 1975, 97: 154 -
17a (Chlorocarbonyl)phenyl ketene and (chlorocarbonyl)benzyl ketene were prepared by a procedure similar to that of Nakanishi:
Nakanishi S.Butler K. Org. Prep. Proced. Int. 1975, 7: 155 -
17b
Roschger P.Fiala W.Stadlbauer W. J. Heterocycl. Chem. 1992, 29: 225 - 18
Kappe T. Farmaco 1999, 59: 309