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■ Preparation of Some New Benzylidenemalononitriles by an S_NAr Reaction: Application to Naphtho[1,2-b]pyran Synthesis

Jason Bloxham, Colin P. Dell,* and Colin W. Smith

*Lilly Research Centre, Eli Lilly and Company, Erl Wood Manor, Windlesham, Surrey GU20 6PH, U.K.

Abstract

The reaction of 4-fluoro-3-nitrobenzylidene malononitrile (3) with piperidine and 1-naphthol yields the addition-elimination product (9) rather than the expected naphtho[1,2-b]pyran (7). This reaction is extended to produce other 3,4-disubstituted benzylidenemalononitriles (10)-(13). These compounds are then reacted with 1-naphthol and 4-methylmorpholine producing the naphtho[1,2-b]pyrans (14)-(17).