Crystal Structure and Hirshfeld Surface Analysis of Acetoacetanilide Based Reaction Products

• Published in: Molecules (Basel, Switzerland) Vol. 25; no. 9; p. 2235
• Main Authors: Naghiyev, Farid N, Cisterna, Jonathan, Khalilov, Ali N, Maharramov, Abel M, Askerov, Rizvan K, Asadov, Khammed A, Mamedov, Ibrahim G, Salmanli, Khaver S, Cárdenas, Alejandro, Brito, Ivan
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 09.05.2020; MDPI
• Subjects: Acetanilides - chemistry; acetoacetanilide; Acetoacetanilides; Crystal structure; Crystallography; Crystallography, X-Ray; Hirshfeld surface analysis; Hydrogen bonds; Malononitrile; Molecular Structure; multicomponent reaction; Piperidine; Reaction products; Structure-Activity Relationship; Surface analysis (chemical); Surface Properties; X-ray analysis; X-ray crystallography; Hirshfeld surface analysis; X-ray analysis; acetoacetanilide; multicomponent reaction
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules25092235

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