title: Expedient synthesis of coumarin-coupled triazoles via 'click chemistry' leading to the formation of coumarin-triazole-sugar hybrids.
abstract: Coumarin-based triazoles were synthesized from 3-azidomethylcoumarin and a terminal acetylenic compound. Uncatalysed thermal conditions result in a mixture of both 1,4- and 1,5-regioisomers or the thermodynamically more stable 1,4-regioisomer, whereas the Cu(I)-catalysed reaction affords only the favourable 1,4-regioisomer. B3LYP/6-31G(d) level of theory has been used to calculate geometry and frequency features of the reactants, transition states (TSs) and products. Computational studies further reveal that 1,4-regioisomeric products are more favourable and also thermodynamically more stable compared to the 1,5-regioisomers.
authors.affiliation: Department of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India.
authors.forename: K Karthik
authors.initials: KK
authors.lastname: Kumar
authors.forename: R Mahesh
authors.initials: RM
authors.lastname: Kumar
authors.forename: V
authors.initials: V
authors.lastname: Subramanian
authors.forename: T Mohan
authors.initials: TM
authors.lastname: Das
mesh_terms: D002241:Carbohydrates / Q000737:chemistry*; D057930:Click Chemistry; D003374:Coumarins / Q000737:chemistry*; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D002241:Carbohydrates; D003374:Coumarins; D014230:Triazoles; C030123:coumarin