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Synthesis 2007(23): 3647-3652
DOI: 10.1055/s-2007-990846
DOI: 10.1055/s-2007-990846
PAPER
© Georg Thieme Verlag Stuttgart · New YorkNew Efficient Synthesis of Pyrido[2,3-c]coumarin Derivatives by Palladium-Catalyzed Heck Cyclization
Further Information
Received
14 August 2007
Publication Date:
29 October 2007 (online)
Publication History
Publication Date:
29 October 2007 (online)

Abstract
Tetrahydropyrido[2,3-c]coumarin derivatives were synthesized by intramolecular radical cyclization and Heck coupling. This method allowed the synthesis of the backbone of the Santiagonamine alkaloid.
Key words
organometallic reagents - radical reactions - Heck coupling - intramolecular cyclization - 3-aminocoumarin
- 1a
Santana L.Uriarte E.Gonzalez-Diaz H.Zagotto G.Soto-Otero R.Mendez-Alvarez E. J. Med. Chem. 2006, 49: 1149 - 1b
Rivkin A.Adams B. Tetrahedron Lett. 2006, 47: 2395 - 1c
Yamaguchi T.Fukuda T.Ishibashi F.Iwao M. Tetrahedron Lett. 2006, 47: 3755 ; and references cited therein - 1d
Burlison JA.Neckers L.Smith AB.Maxwell A.Blagg BSJ. J. Am. Chem. Soc. 2006, 128: 15529 - 2a
Gellert M.O’Dea MH.Itoh T.Tomizawa ZI. Proc. Natl. Acad. Sci. U.S.A. 1976, 73: 4474 - 2b
Levine C.Hiasa H.Marians KJ. Biochim. Biophys. Acta 1998, 1400: 29 - 3
Valencia E.Patra A.Freyer AJ.Shamma M.Fajardo V. Tetrahedron Lett. 1984, 25: 3163 - 4
Lewis WH,Stonard RJ,Porras-Reyes B,Mustoe TA, andThomas A. inventors; US Patent 5156847. ; Chem. Abstr. 1992, 117, 245630t - 5a
Khan MA.Gemal AL. J. Heterocycl. Chem. 1977, 14: 1009 - 5b
Tabakovic K.Tabakovic I.Trkovnik M.Juric A.Trinajstic N. J. Heterocycl. Chem. 1980, 17: 801 - 5c
Sagi M.Wada K.Konno S.Yamaka H. Heterocycles 1990, 30: 1009 - 6a
Majumdar KC.Muhuri S.Rahaman H.Islam R.Roy B. Chem. Lett. 2006, 35: 1430 - 6b
Majumdar KC.Rahaman H.Roy B. Lett. Org. Chem. 2006, 3: 526 - 6c
Majumdar KC.Chattopadhyay B. Synth. Commun. 2006, 36: 3125 - 6d
Majumdar KC.Mukhopadhyay PP.Basu PK. Synth. Commun. 2005, 35: 1291 - 6e
Majumdar KC.Chattopadhyay SK. Tetrahedron Lett. 2004, 45: 6871 - 6f
Majumdar KC.Bhattacharyya T. Tetrahedron Lett. 2001, 42: 4231 - 7a
Majumder KC.Alam S. Org. Lett. 2006, 8: 4059 - 7b
Curran DP. In Comprehensive Organic Synthesis Vol. 4:Trost BM.Fleming I. Pergamon; Oxford: 1991. p.715-779 - 7c
Fossey J.Lefort D.Sorba J. Free Radicals in Organic Synthesis Wiley; Chichester: 1995. - 7d
Motherwell WB.Crich D. Free Radical Chain Reaction in Organic Synthesis Academic Press; London: 1992. - 7e
Radicals in Organic Synthesis
Renaud P.Sibi MP. Wiley-VCH; Weinheim: 2001. - 7f
Giese B.Kopping B.Goble T.Dickhaut J.Thoma G.Kulicke KJ.Trach F. Org. React. 1996, 48: 301 - 7g
Jasperse CP.Curran DP.Fevig TL. Chem. Rev. 1991, 91: 1237 - 9
Lee S.Robinson G. Process Development: Fine Chemicals from Gram to Kilograms Oxford University Press; New York: 1995. - 10a
Gazith M.Noys RM. J. Am. Chem. Soc. 1955, 77: 6091 - 10b
Gardner IJ.Noyes RM. J. Am. Chem. Soc. 1961, 83: 2409 - 11a
Dean FM.Robertson A.Whalley WB. J. Chem. Soc. 1950, 895 - 11b
Trivedi KN.Sethna S. J. Org. Chem. 1960, 25: 1817 - 12
Kuroda T.Suzuki F. Tetrahedron Lett. 1991, 32: 6915
References
For a detailed report on the toxicity of tin reagents, see: Occupational Exposure to Organotin Compounds, US Department of Health Education and Welfare: Washington D.C., Nov. 1976.