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Crystal Structure and Hirshfeld Surface Analysis of Acetoacetanilide Based Reaction Products

Farid N. Naghiyev, Jonathan Cisterna, Ali N. Khalilov, Abel M. Maharramov, Р.К. Аскеров, Kh. A. Asadov, I. G. Mamedov, Khaver S. Salmanli, Alejandro Cárdenas, Iván Brito

2020Molecules26 citationsDOIOpen Access PDF

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-N-phenyl-4-(yridine-4-yl)-6-(thiophen-2-yl)-3,4-dihydro-2H-pyran-3-carboxamide 2, 5-cyano-2-hydroxy-2-methyl-6-oxo-N-phenyl-4-(thiophen-2-yl)piperidine-3-carboxamide 4 and 2-(8-amino-7,8a-dicyano-1-imino-4a-methyl-3-oxo-2-phenyl-1,3,4,4a,5,8a-hexahydroisoquinolin-6(2H)-ylidene)-N-phenylacetamide 9.

Topics & Concepts

MalononitrilePiperidineCrystal structurePyranChemistryYield (engineering)CarboxamideBicyclic moleculeStereochemistryMedicinal chemistryCrystallographyOrganic chemistryMaterials scienceCatalysisMetallurgySynthesis of heterocyclic compoundsMulticomponent Synthesis of HeterocyclesSynthesis and biological activity
Crystal Structure and Hirshfeld Surface Analysis of Acetoacetanilide Based Reaction Products | Litcius