Journal of Heterocyclic Chemistry

Synthesis and reactions of 1??[1??oxido??2??(3, 4)??pyridinyl]??2??methyloxiranes with nitrogen nucleophiles

K Avasthi, EE Knaus

Index: Avasthi, Kamlakar; Knaus, Edward E. Journal of Heterocyclic Chemistry, 1981 , vol. 18, p. 375 - 382

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Citation Number: 3

Abstract

Abstract Reaction of 2 (3, 4)-pyridinecarboxaldehydes (5) with ethylidenetriphenylphosphorane afford a mixture of stereoisomers Z-(6) and E-1-[2 (3, 4)- pyridinyl]-1-propenes (7). m-Chloroperbenzoic acid oxidation of 6 and 7 yields a 60: 40 mixture of Z-(8) and E-1-[1-oxido-2 (3, 4)-pyridinyl]-2-methyloxiranes (9). The regiospecific reaction of Z-isomers 8a-c with cyclic amines as piperidine give rise to threo-1-hydroxy-1-[ ...