title: Catalyst-free multicomponent synthesis of novel adamantyl-containing tetrahydropyrimidine carboxylates.
abstract: [Formula: see text]-Enaminoesters were generated in situ by the reaction of aliphatic or aromatic primary amines to electron-deficient alkynes, dimethyl acetylenedicarboxylate, and methyl propiolate. [Formula: see text]-Enaminoesters thus formed were reacted with 1-adamantanamine and formaldehyde in methanol to give novel molecular hybrids: dimethyl 3-((3s,5s,7s)-adamantan-1-yl)-1-(alkyl/aralkyl/aryl)-1,2,3,4-tetrahydropyrimidine-5,6-dicarboxylates (5a-j) and methyl 3-((3s,5s,7s)-adamantan-1-yl)-1-(alkyl/aralkyl/aryl)-1,2,3,4-tetrahydropyrimidine-5-carboxylates (9a-j). The structures of the molecular hybrids have been established based on the spectral and analytical data. Structural confirmation of the products was done by X-ray crystallography of 5d as a representative product of the series.
authors.affiliation: Organic Research Laboratory, Department of Chemical Science, Assam Don Bosco University, Airport Road, Azara, Guwahati, 781017, India.
authors.forename: Utpalparna
authors.initials: U
authors.lastname: Kalita
authors.affiliation: Organic Research Laboratory, Department of Chemical Science, Assam Don Bosco University, Airport Road, Azara, Guwahati, 781017, India.
authors.forename: Shunan
authors.initials: S
authors.lastname: Kaping
authors.affiliation: Organic Research Laboratory, Department of Chemical Science, Assam Don Bosco University, Airport Road, Azara, Guwahati, 781017, India. jnvishwakarma@rediffmail.com.
authors.forename: Jai Narain
authors.initials: JN
authors.lastname: Vishwakarma
mesh_terms: D000547:Amantadine / Q000737:chemistry; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D015394:Molecular Structure
chemical_list: D002264:Carboxylic Acids; D000547:Amantadine
keywords: -Enaminoesters; 1-Adamantanamine; Cyclization; Heterocycles; MCRs; Multicomponent reactions; Tetrahydropyrimidine