Expedient synthesis of coumarin-coupled triazoles via 'click chemistry' leading to the formation of coumarin-triazole-sugar hybrids.
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.
Kumar
K Karthik
KK
Department of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India.
Kumar
R Mahesh
RM
Subramanian
V
V
Das
T Mohan
TM
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
D002241:Carbohydrates; D003374:Coumarins; D014230:Triazoles; C030123:coumarin