Synthesis of pyrrolizin-3-ones by flash vacuum pyrolysis of pyrrol-2-ylmethylidene Meldrum's acid derivatives and 3-(pyrrol-2-yl) propenoic esters

SE Campbell, MC Comer, PA Derbyshire…

Index: Campbell, Shirley E.; Comer, Murray C.; Derbyshire, Paul A.; Despinoy, Xavier L. M.; McNab, Hamish; Morrison, Roderick; Sommerville, Craig C.; Thornley, Craig Journal of the Chemical Society - Perkin Transactions 1, 1997 , # 15 p. 2195 - 2202

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Citation Number: 2

Abstract

Monosubstituted pyrrolizin-3-ones 1 with substituents at the 1-, 5-, 6-or 7-positions are prepared in excellent yield by flash vacuum pyrolysis (FVP) of appropriate Meldrum's acid derivatives 2. The mechanism involves formation of the pyrrol-2-ylmethylideneketene 29, which can also be generated thermally from 3-(pyrrol-2-yl) propenoate esters (eg 30). This alternative route has been used to make a range of 2-substituted pyrrolizin-3-ones, again ...