An efficient and novel approach to the synthesis of 3, 4, 5, 6-tetraphenyl-2 (1H)-pyridinone

RL Eagan, MA Ogliaruso…

Index: Eagan, Robert L.; Ogliaruso, Michael A. Journal of Organic Chemistry, 1986 , vol. 51, # 9 p. 1544 - 1547

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Citation Number: 8

Abstract

The reaction of tetracyclone (la) with sodium azide under acidic conditions was found to give 3, 4, 5, 6-tetraphenyL2 (1H)-pyridinone (2a) in 90% isolated yield. The reaction does not proceed by a Schmitt mechanism. By adjusting the reaction conditions, the intermediate 1, 5, 7, 8tetraphenyl-2, 3, 4-triazabicyclo [3.3. 0]~~-2, 7-dien-6-one (3a) was isolated in 94% yield. Treatment of 3a under acidic conditions resulted in loss of nitrogen and formation of 2a. ...