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.
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
Tienan
T
Jin
Fukuzou
F
Kitahara
Shin
S
Kamijo
Yoshinori
Y
Yamamoto
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