Chemistry of Heterocyclic Compounds p. 304 - 311 (1990)
Update date:2022-08-05
Topics:
Khlebnikov, A. F.
Kostik, E. I.
Kostikov, R. R.
Bespalov, V. Ya.
Pyridinium dichloromethylides, generated from substituted pyridines and dichlorocarbene, react endo-stereoselectively with dimethyl maleate to give substituted 3,3-dichloro-1,2,3,8a-tetrahydroindolizine-1,2-dicarboxylic acid dimethyl esters; the latter compounds are readily dehydrochlorinated and dehydrogenated to give the corresponding indolizine derivatives.Reaction of 3-substituted pyridines with dichlorocarbene and dimethyl maleate leads predominantly to the formation of 8-substituted indolizines.Cycloaddition of 4-picolinium dichloromethylide to unsymmetrical dipol arophiles occurs regioselectively.The observed selectivity in these reactions is consistent with predictions made on the basis of PMO theory.
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