Synlett 2009(14): 2366-2370  
DOI: 10.1055/s-0029-1217797
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© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Highly Functionalized Spirobenzofuranols and Spirobenzofuranones by Baylis-Hillman Reaction

K. Karthikeyan, P. T. Perumal*
Organic Chemistry Division, Central Leather Research Institute, Adyar, Chennai 600020, India
Fax: +91(44)24911589; e-Mail: ptperumal@gmail.com;
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Publication History

Received 25 May 2009
Publication Date:
06 August 2009 (online)

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Abstract

Baylis-Hillman reaction of salicylaldehydes with N-aryl/alkyl maleimides under neat conditions for the synthesis of chromenes resulted in an unusual cyclization to form spirobenzofuranol derivatives in moderate to good yield. PDC oxidation of the resultant products yielded the corresponding spirobenzofuranone derivatives.

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