Reactions with α‐substituted cinnamonitriles. A novel synthesis of hexa‐substituted pyridines

Abstract

Whereas acetoacetanilide (II) reacted with α‐cyano‐ and α‐benzoylcinnamonitrile derivatives Ia‐e to give hexa‐substituted pyridines III and V, it reacted with α‐carboxamido‐ and α‐thiocarboxamidocinnammonitrile derivatives If‐h to afford penta‐substituted pyridines VI. One mole of acetonedicarboxylic acid dianilide (VII) reacted with two moles of each of α‐cyano‐ and α‐thiocarboxamidocinnamonitriles Ia,b,f,g to yield the dipyridyl ketones VIII and IX, respectively. On the other hand, α‐benzoyl‐ and α‐ethoxycarbonylcinnamonitriles Ic,d,i,j reacted with VII in equimolecular ratio to give the pyran derivaties X and XI, respectively. Several schemes were proposed to illustrate reactions steps. The structures of the synthesized compounds were proved by chemical and spectral methods.

Reactions of carbonyl compounds with α,β-unsaturated nitriles as a convenient pathway to carbo- and heterocycles

“…The intramolecular cyclisation of the intermediate adducts affords hydrogenated pyridones 313 190 and 314. 191 It has been shown 192 that the reaction of cyanoacetylhydrazine 315 with the arylidenemalononitriles 42 gives rise to 1-amino-2(1H)-pyridones 316.…”

Crystal Structure and Hirshfeld Surface Analysis of Acetoacetanilide Based Reaction Products

“…Pyridone, piperidine, pyran, and isoquinoline moieties are functional components of various natural products [ 1 , 2 , 3 ], pharmaceuticals [ 4 , 5 , 6 ], and biologically active compounds [ 7 , 8 , 9 ]. Two-component [ 10 ] and multicomponent [ 11 , 12 , 13 ] tandem transformations leading to these heterocyclic systems are particularly attractive from the point of view of diversity-oriented synthesis because of their modularity and rapid buildup of molecular complexity. In this article, we disclose a high-yielding synthesis of a structurally novel bicyclic heterocycle from two simple starting materials.…”