Structural elucidation of propargylated products of 3-substituted-1,2,4-triazole-5-thiols by NMR techniques.
Propargylation of 3-substituted-1,2,4-triazole-5-thiols, which predominantly exist as their thione tautomers, was carried out with the view to synthesize different heterocycles and study their biological activity. Three different products namely, a mono S-propargyl and two S,N-dipropargyl regioisomers, arising from N1/N2 substitution, were isolated and characterized. Unambiguous structural elucidation of the regioisomers of S,N-dipropargyl derivatives was achieved by means of (13)C-(1)H HMBC technique. The proportion of the regioisomers was found to vary with the substituent on the 1,2,4-triazole thiols. No product corresponding to N4 substitution was isolated from any of the reactions carried out.
Division of Organic Chemistry, National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411008, India.
Preeti M
PM
Chaudhary
Sayalee R
SR
Chavan
M
M
Kavitha
Shailaja P
SP
Maybhate
Sunita R
SR
Deshpande
Anjali P
AP
Likhite
P R
PR
Rajamohanan
D000480:Alkynes / Q000737:chemistry*; D002247:Carbon Isotopes; D002625:Chemistry, Organic / Q000379:methods; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D015394:Molecular Structure; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D014230:Triazoles / Q000737:chemistry*
D000480:Alkynes; D002247:Carbon Isotopes; D013438:Sulfhydryl Compounds; D014230:Triazoles