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Synthesis 2008(11): 1753-1756
DOI: 10.1055/s-2008-1072581
DOI: 10.1055/s-2008-1072581
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Venlafaxine from Azadiene via a Hetero-Diels-Alder Approach: New Microwave-Assisted Transketalization and Hydroxymethylation Reactions
Further Information
Received
5 February 2008
Publication Date:
07 April 2008 (online)
Publication History
Publication Date:
07 April 2008 (online)

Abstract
Hetero-Diels-Alder (HDA) methodology has been applied to the synthesis of Venlafaxine taking advantage of a novel MW-assisted transketalization and hydroxymethylation reaction.
Key words
1,3-aminol - hetero-Diels-Alder reaction - MAOS - Venlafaxine - transketalization
-
1a
Panunzio M.Vicennati P. In Recent Research Development in Organic Chemistry Vol. 6, Part II:Pandalai SG. Transworld Research Network; Trivandrum India: 2002. p.683-707 -
1b
Ghosez L.Bayard P.Nshimyumukiza P.Gouverneur V.Sainte F.Beaudegnies R.Rivera M.Frisque-Hesbain AM.Wynants C. Tetrahedron 1995, 51: 11021 -
1c
Barluenga J.Suarez-Sobrino A.Lopez LA. Aldrichimica Acta 1999, 32: 4 -
1d
Jayakumar S.Ishar MP.Mahajan MP. Tetrahedron 2002, 58: 379 -
2a
Boger DL.Weinreb SM. Hetero Diels-Alder Methodology in Organic Synthesis Vol. 47: Academic Press; New York: 1987. -
2b
Gilchrist TL.Rocha Gonsalves AMdA.Pinho e Melo TMVD. Pure Appl. Chem. 1996, 68: 859 -
2c
Jnoff E.Ghosez L. J. Am. Chem. Soc. 1999, 121: 2617 -
2d
Ntirampebura D.Ghosez L. Tetrahedron Lett. 1999, 40: 7079 -
2e
Ntirampebura D.Ghosez L. Synthesis 2002, 2043 -
2f
Jörgensen KA. Angew. Chem. Int. Ed. 2000, 39: 3558 -
2g
Kumar A. Chem. Rev. 2001, 101: 1 -
2h
Roberson M.Jepsen AS.Jörgensen KA. Tetrahedron 2001, 57: 907 - 3
Lait SM.Rankic DA.Keay BA. Chem. Rev. 2007, 107: 767 -
4a
Panunzio M.Rossi K.Tamanini E.Campana E.Martelli G. Tetrahedron: Asymmetry 2004, 15: 3489 -
4b
Panunzio M.Tamanini E.Bandini E.Campana E.D’Aurizio A.Vicennati P. Tetrahedron 2006, 62: 12270 -
5a
Chavan SP.Khobragade DA.Kamat SK.Sivadasan L.Balakrishnan K.Ravindranathan T.Gurjar MK.Kalkote UR. Tetrahedron Lett. 2004, 45: 7291 -
5b
Davies HML.Ni AW. Chem. Commun. 2006, 3110 -
5c
Kavitha CV.Basappa B.Swamy SN.Mantelingu K.Doreswamy S.Sridhar MA.Prasad JS.Rangappa KS. Bioorg. Med. Chem. 2006, 14: 2290 -
5d
Kavitha CV.Lakshmi S.Basappa B.Mantelingu K.Sridhar MA.Prasad JS.Rangappa KS. J. Chem. Crystallogr. 2005, 35: 957 -
5e
Kavitha CV.Rangappa KS. Bioorg. Med. Chem. Lett. 2004, 14: 3279 -
5f
Yardley JP.Husbands GEM.Stack G.Butch J.Bicksler J.Moyer JA.Muth EA.Andree T.Fletcher H.James MNG.Sielecki AR. J. Med. Chem. 1990, 33: 2899 - 6
Bandini E.Martelli G.Spunta G.Bongini A.Panunzio M. Synlett 1999, 1735 - 7
Jorgensen KA. Eur. J. Org. Chem. 2004, 2093 - 8
Panunzio M.Bandini E.D’Aurizio A.Xiao Z. Synthesis 2007, 2060 -
9a
Bongini A.Panunzio M.Piersanti G.Bandini E.Martelli G.Spunta G.Venturin A. Eur. J. Org. Chem. 2000, 2379 -
9b
Bongini A.Panunzio M. Eur. J. Org. Chem. 2006, 972 - 10
Huang Y.Rawal VH. J. Am. Chem. Soc. 2002, 124: 9662 - 11
Bongini A.Panunzio M.Tamanini E.Martelli G.Vicennati P.Monari M. Tetrahedron: Asymmetry 2003, 14: 993