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Synthesis 2008(1): 101-109  
DOI: 10.1055/s-2007-990929
PAPER
© Georg Thieme Verlag Stuttgart · New York

Application of Primary Allylamine Derivatives of Baylis-Hillman Adducts to Heterocyclic Synthesis: Generation of 5-Benzyl-4(3H)-pyrimidinones and 2-Benzylidene-2,3-dihydropyrrolizin-1-ones [1]

Somnath Nag, Sudharshan Madapa, Sanjay Batra*
Medicinal and Process Chemistry Division, Central Drug Research Institute, PO Box 173, Lucknow 226 001, India
Fax: +91(522)2623405, 2623938; e-Mail: batra_san@yahoo.co.uk;
Further Information

Publication History

Received 5 September 2007
Publication Date:
28 November 2007 (online)

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Abstract

The applications of the primary allylamines obtained from the acetyl derivative of Baylis-Hillman adducts of acrylate for the synthesis of heterocycles using robust reactions are described. In the first strategy, a one-pot synthesis of 5-benzyl-4(3H)-pyrimidinones have been achieved via N-formylation of the amines in the presence of neat formamide followed by ammonium formate-mediated cyclization. These pyrimidinones have been demonstrated to be excellent precursor to the 4-pyridinamine derivatives. In the second strategy, the synthesis of 2-benzylidene-2,3-dihydropyrrolizin-1-ones have been accomplished via treatment of allylamine with dimethoxyfuran followed by saponification and PPA-mediated intramolecular cyclization.

Key words

Baylis-Hillman - formamide - N-formylation - primary allyl amine - 4(3H)-pyrimidinone - 4-pyridinamine - 2,3-dihydro-1H-pyrrolizin-1-one

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CDRI Communication No. 7367.

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CDRI Communication No. 7367.