Metal triflate catalyzed reactions of alkenes, NBS, nitriles, and TMSN3: synthesis of 1,5-disubstituted tetrazoles.
A versatile and highly efficient protocol for the synthesis of 1,5-disubstituted tetrazoles has been developed by metal triflate catalyzed one-pot reaction of alkenes, NBS, nitriles, and TMSN3. Among the metal triflates, Zn(OTf)2 was found to be the best catalyst. Use of different combinations of alkenes and nitriles generate a variety of 1,5-disubstituted tetrazoles containing an additional alpha-bromo functionality of the N1-alkyl substituent.
Hajra
Saumen
S
Department of Chemistry, Indian Institute of Technology, Kharagpur 721 302, India. shajra@chem.iitkgp.ernet.in
Sinha
Debarshi
D
Bhowmick
Manishabrata
M
D000475:Alkenes / Q000737:chemistry*; D001974:Bromosuccinimide / Q000737:chemistry*; D002384:Catalysis; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008670:Metals / Q000737:chemistry*; D009570:Nitriles / Q000737:chemistry*; D017550:Spectroscopy, Fourier Transform Infrared; D013237:Stereoisomerism; D013777:Tetrazoles / Q000138:chemical synthesis*; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
D000475:Alkenes; D008670:Metals; D009570:Nitriles; D013777:Tetrazoles; D014297:Trimethylsilyl Compounds; D001974:Bromosuccinimide