1023749-37-2Relevant academic research and scientific papers
A practical route to 2,3-di-/1,2,3-trisubstituted indolizines from α-EWG ketene S,S-acetals and their application in bis(1-indolizinyl) methane synthesis
Sun, Shaoguang,Wang, Mang,Deng, Hongxia,Liu, Qun
, p. 573 - 583 (2008)
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. Georg Thieme Verlag Stuttgart.
