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 2008(6): 871-874
DOI: 10.1055/s-2008-1032209
DOI: 10.1055/s-2008-1032209
PAPER
© Georg Thieme Verlag Stuttgart · New York
Reactions of N-Acyl Imines with Dihydropyrans
Further Information
Received
17 September 2007
Publication Date:
28 February 2008 (online)
Publication History
Publication Date:
28 February 2008 (online)

Abstract
A series of dihydropyranyl acetamides was synthesized by the TFA-catalyzed reaction of dihydropyrans with N-acyl imines.
Key words
N-acyl imines - dihydropyrans - dihydropyranyl acetamides - Mannich reaction - cycloaddition
- 1
Petrini M.Torregiani E. Synthesis 2007, 159 - 2
Weinreb SM.Scola PM. Chem. Rev. 1989, 89: 1525 - 3
Gizecki P.Youcef RA.Poulard C.Dhal R.Dujardin G. Tetrahedron Lett. 2004, 45: 9589 - 4
Gizecki P.Dhal R.Poulard C.Gosselin P.Dujardin G. J. Org. Chem. 2003, 68: 4338 - 5
Gizecki P.Dhal R.Toupet L.Dujardin G. Org. Lett. 2000, 2: 585 - 6
Kobayashi S.Matsubara R.Nakamura Y.Kitagawa H.Sugiura M. J. Am. Chem. Soc. 2003, 125: 2507 - 7
Schmidt RR. Angew. Chem., Int. Ed. Engl. 1969, 8: 602 - 8 Chmielewski has reported the formation of related bicyclic structures from the reactions of glycals with trichloroacetyl isocyanate, see:
Chmielewski M.Kaluza Z. J. Org. Chem. 1986, 51: 2395 - 9
Ikeda K.Morimoto T.Sekiya M. Chem. Pharm. Bull. 1980, 28: 1178 - 10
Oguri H.Oomura A.Tanabe S.Hirama M. Tetrahedron Lett. 2005, 46: 2179 - 11
Kupfer R.Meier S.Würthwein EU. Synthesis 1984, 688 -
12a
Fuchs JR.Funk RL. Org. Lett. 2005, 7: 677 -
12b
Lellouche J.-P.Koeller S. J. Org. Chem. 2001, 66: 693 -
12c
Unterhalt B.Bause G. Pharmazie 1998, 53: 231 -
12d
Moriguchi T.Endo T.Takata T. J. Org. Chem. 1995, 60: 3523 -
12e
Hojo M.Masuda R.Sakaguchi S.Takagawa M. Synthesis 1986, 1016 -
12f
Barrett AGM.Betts MJ.Fenwick A. J. Org. Chem. 1985, 50: 169 - 13
Takaki K.Yamada M.Negoro K. J. Org. Chem. 1982, 47: 5246 - 15
Sheldrick GM. SHELXS-97 University of Göttingen; Göttingen: 1997.
References
Crystallographic data (excluding structure factors) for structure 4d reported in this paper have been deposited with the Cambridge crystallographic Data Centre as supplementary publication number CCDC 657468. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: +44 (1223)336 033; E-mail: deposit@ccdc.cam.ac.uk].