Synthesis of 5-substituted 1H-tetrazoles by the copper-catalyzed [3+2] cycloaddition of nitriles and trimethylsilyl azide.
The copper-catalyzed [3+2] cycloaddition between various nitriles and trimethylsilyl azide in DMF/MeOH produced the corresponding 5-substituted 1H-tetrazoles in good to high yields. It was proposed that the reaction proceeds through the formation in situ of a copper azide species and subsequent [3+2] cycloaddition with the nitriles. Furthermore, we found that a copper and triethylamine combined catalyst also promoted the cycloaddition of nitriles and trimethylsilyl azide to afford the 5-substituted 1H-tetrazoles at relatively low reaction temperatures. The copper azide species would be formed by reaction of the copper catalyst with Et(3)NHN(3) generated in situ.
Jin
Tienan
T
Department of Chemistry, Graduate School of Science, Tohoku University, 6-3 Aramaki Aza Aoba, Aoba-ku, Sendai 980-8578, Japan. tjin@mail.tains.tohoku.ac.jp
Kitahara
Fukuzou
F
Kamijo
Shin
S
Yamamoto
Yoshinori
Y
D001386:Azides / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D007477:Ions / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D008970:Molecular Weight; D009570:Nitriles / Q000737:chemistry*; D011108:Polymers / Q000737:chemistry; D012997:Solvents; D013777:Tetrazoles / Q000138:chemical synthesis* / Q000737:chemistry; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
D001386:Azides; D007477:Ions; D009570:Nitriles; D011108:Polymers; D012997:Solvents; D013777:Tetrazoles; D014297:Trimethylsilyl Compounds; C045574:1H-tetrazole; D003300:Copper