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.
Chaudhary
Preeti M
PM
Division of Organic Chemistry, National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411008, India.
Chavan
Sayalee R
SR
Kavitha
M
M
Maybhate
Shailaja P
SP
Deshpande
Sunita R
SR
Likhite
Anjali P
AP
Rajamohanan
P R
PR
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