Crystal Structure and Hirshfeld Surface Analysis of Acetoacetanilide Based Reaction Products

Abstract

We report an unprecedented multicomponent reaction of acetoacetanilide with malononitrile leading to a structurally novel bicyclic product (9) in a high yield. The structure has been confirmed by X-ray crystallography and comparative Hirshfeld surface analysis of 5-cyano-2-hydroxy-2-methyl-<i>N</i>-phenyl-4-(yridine-4-yl)-6-(thiophen-2-yl)-3,4-dihydro-2<i>H</i>-pyran-3-carboxamide <b>2</b>, 5-cyano-2-hydroxy-2-methyl-6-oxo-<i>N</i>-phenyl-4-(thiophen-2-yl)piperidine-3-carboxamide <b>4</b> and 2-(8-amino-7,8a-dicyano-1-imino-4a-methyl-3-oxo-2-phenyl-1,3,4,4a,5,8a-hexahydroisoquinolin-6(2<i>H</i>)-ylidene)-<i>N</i>-phenylacetamide <b>9</b>.