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Synthesis of 5‐Substituted 1 H ‐Tetrazoles by the Copper‐Catalyzed [3+2] Cycloaddition of Nitriles and Trimethylsilyl Azide
Author(s) -
Jin Tienan,
Kitahara Fukuzou,
Kamijo Shin,
Yamamoto Yoshinori
Publication year - 2008
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.200800085
Subject(s) - cycloaddition , trimethylsilyl azide , azide , chemistry , copper , triethylamine , catalysis , trimethylsilyl , medicinal chemistry , organic chemistry
The copper‐catalyzed [3+2] cycloaddition between various nitriles and trimethylsilyl azide in DMF/MeOH produced the corresponding 5‐substituted 1 H ‐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 1 H ‐tetrazoles at relatively low reaction temperatures. The copper azide species would be formed by reaction of the copper catalyst with Et 3 N⋅HN 3 generated in situ.