The Journal of Organic Chemistry

Reactions of trimethylsilyl azide with heterocumulenes

O Tsuge, S Urano, K Oe

Index: Tsuge, Otohiko; Urano, Satoshi; Oe, Koji Journal of Organic Chemistry, 1980 , vol. 45, # 25 p. 5130 - 5136

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Citation Number: 55

Abstract

Trimethylsilyl azide (TMSA) reacted with aryl isocyanates to give arylcarbamoyl azides, l-aryl- 5 (4H)-tetrazolinones, and/or l-aryl-4-(arylcarbamoyl)-5 (4H)-tetrazolinones, whose yields were dependent on the reaction conditione. The reaction between TMSA and benzoyl or thiobenzoyl isocyanates provides a facile method for the preparation of 5-aryl-3-hydroxy-l, 2, 4-oxadiazoles or-1, 2, 4-thiadiazoles, respectively. However, with phenyl or benzoyl ...

~10%

~90%

~81%

~97%

~30%

~28%

~10%

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