Tetrahedron

Photochemistry of benzene and quinoxaline fused Δ 2-1, 2, 3-triazolines and their trapping products

YJ Chen, HC Hung, CK Sha, WS Chung

Index: Chen, Yu-Jen; Hung, Hao-Chih; Sha, Chin-Kang; Chung, Wen-Sheng Tetrahedron, 2010 , vol. 66, # 1 p. 176 - 182

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Citation Number: 6

Abstract

The benzene and quinoxaline fused Δ2-1, 2, 3-triazolines 1a and 1b were synthesized in good yields using Knoevenagel condensation and intramolecular 1, 3-dipolar cycloaddition as two of the key reactions. Photolysis (254nm) of Δ2-1, 2, 3-triazoline 1a or 1b in acetonitrile led to the homolytic cleavage of nitrogen that generated diethyl diazomalonate 7, highly reactive intermediates aziridines 8a, b, and isoindoles B. The latter two species ...