Abstract
An easy synthesis of 2,3-di-/1,2,3-trisubstituted indolizines has been developed via a formal [3+2] annulation of α-EWG ketene S ,S -acetals with 2-pyridine-/2-quinolinecarbaldehyde. The disubstituted products are formed via an intramolecular aza-Michael addition and subsequent elimination of acetic acid, followed by desulfenylation assisted by acetic acid, whereas the trisubstituted products are obtained via a similar conjugate addition followed by elimination of alkanethiol. This strategy has been applied to the synthesis of bis(1-indolizinyl)methanes by the condensation of a 2,3-disubstituted indolizine with aldehydes/ketones in the presence of a catalytic amount of BF3 ·OEt2 .
Key words
indolizines - α-EWG ketene S ,S -acetals - bis(1-indolizinyl)methanes - annulation - condensation
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