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Paper | Regular issue | Vol 65, No. 7, 2005, pp.1629-1639
Published online, 10th May, 2005
DOI: 10.3987/COM-05-10423
Synthesis and Properties of 3-Arylcyclohepta[4,5]pyrrolo[1,2-a]-1,3,5-triazine-2,4(3H)-diones and Related Compounds: Photo-induced Autorecycling Oxidation of Amines

Makoto Nitta,* Tomoyuki Morito, Yuhki Mitsumoto, and Shin-ichi Naya

*Department of Chemistry, School of Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo 169-8555, Japan

Abstract

3-Phenyl- and 3-(4-nitrophenyl)cyclohepta[4,5]pyrrolo[1,2-a]-1,3,5- triazine-2,4(3H)-diones and the corresponding arylimino derivatives (5a,b) and (6a,b) were synthesized by the reaction of (1-azaazulen-2-yl)imino- triphenylphosphorane with aryl isocyanates and subsequent heterocyclization reaction with a second isocyanate. Related cation (11a), which was derived from methylation of 5a, is also prepared. The electrochemical reduction of these compounds exhibited more negative reduction potentials as compared with the related compounds. Some of these compounds underwent a photo-induced autorecycling oxidation toward some amines to give the corresponding imines in more than 100% yield.