154367-56-3Relevant academic research and scientific papers
Synthesis of pyrrolizin-3-ones by flash vacuum pyrolysis of pyrrol-2-ylmethylidene Meldrum's acid derivatives and 3-(pyrrol-2-yl)propenoic esters
Campbell, Shirley E.,Comer, Murray C.,Derbyshire, Paul A.,Despinoy, Xavier L. M.,McNab, Hamish,Morrison, Roderick,Sommerville, Craig C.,Thornley, Craig
, p. 2195 - 2202 (2007/10/03)
Monosubstituted pyrrolizin-3-ones 1 with substituants 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 (e.g. 30). This alternative route has been used to make a range of 2-substituted pyrrolizin-3-ones, again in excellent yield. The 3-oxo-3H-pyrrolizine-2-carboxylic acid 42 could not be made in this way owing to facile decarboxylation to pyrrolizinone 1, and extension to the formation of the azaazulenone 48 was again unsuccessful.
New Chemistry of Pyrrolizin-3-one: a Concise Route to 3,8-Didehydroheliotridin-5-one
McNab, Hamish,Thornley, Craig
, p. 1570 - 1571 (2007/10/02)
1-Substituted 1,2-dihydropyrrolizin-3-ones can be obtained from pyrrolizin-3-one 2 by conjugate nucleophilic addition or electrophilic addition reactions; the 1-chloro compound 9 obtained by the latter method is used as a key intermediate in a six-step synthesis of the title compound 3 from 4-acetoxymethylpyridine-N-oxide.
