Synthesis of fused furans by gas-phase pyrolysis of 2-allyloxyarylpropenoic esters

…, JIG Cadogan, H McNab, AD MacPherson…

Index: Black, Michael; Cadogan; McNab, Hamish; MacPherson, Andrew D.; Roddam, V. Peter; Smith, Carol; Swenson, Helen R. Journal of the Chemical Society - Perkin Transactions 1, 1997 , # 17 p. 2483 - 2493

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Citation Number: 30

Abstract

Flash vacuum pyrolysis of 2-allyloxypropenoic esters (eg 7) gives benzo [b] furans (eg 32) in synthetically useful yields by sequential generation of a phenoxyl radical, cyclisation and ejection of the carboxylic ester function as a free radical leaving group. The method is compatible with a range of substituents on either the benzene ring or the propenoate chain, and is particularly effective for 2-substituted benzo [b] furans. The natural products 5- ...

~38%

~92%

~82%

~72%

~60%

~94%

~21%

~84%

~12%

~52%

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