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Paper | Regular issue | Vol 48, No. 12, 1998, pp.2581-2592
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8349
2-Bromo-2-nitropropane/Zn Promoted Reductive Cyclizations of ortho-Carbonyl, Imino, or Azo Substituted Nitrobenzenes

Byeong Hyo Kim,* Yoon Seok Lee, Woong Kwon, Youngoo Jin, Jung Ae Tak, Young Moo Jun, Woonphil Baik, and Byung Min Lee

*Department of Chemistry, Kwangwoon University, 447-1, Wolgye-Dong Nowon-ku, Seoul, 139-701, Korea


Under the mild conditions, reductive cyclizations of 2-nitrobenzaldehydes, 2’-nitroacetophenone, and N-(2-nitrobenzylidene)anilines were accomplished in the presence of 2-bromo-2-nitropropane/Zn in methanolic solution. Under the similar conditions in MeOH/CH2Cl2, o-nitro-substituted phenylazobenzenes have been converted into 2-aryl-2H-benzotriazoles via reductive cyclizations that are widely used as UV absorbers. Synthesis and mechanistic details are discussed.