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Synthesis 2010(8): 1315-1320  
DOI: 10.1055/s-0029-1219276
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Concise Synthesis of Pyrimido-azocine Derivatives via Aza-Claisen Rearrangement and Intramolecular Heck Reaction

K. C. Majumdar*, Shovan Mondal, Debankan Ghosh, Buddhadeb Chattopadhyay
Department of Chemistry, University of Kalyani, Kalyani 741235, WB, India
e-Mail: kcm_ku@yahoo.co.in;
Further Information

Publication History

Received 14 December 2009
Publication Date:
25 January 2010 (online)

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Abstract

An expedient approach involving BF3˙OEt2-catalyzed aza-Claisen rearrangement and palladium-catalyzed intramolecular Heck reaction for the synthesis of pyrimidine-fused azocine derivatives is described. The mechanistic interpretation of the plausible mode of cyclization is also described.

Key words

uracil - aza-Claisen rearrangement - azocine - Heck reaction

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