2-bromo-2-nitropropane/Zn promoted reductive cyclizations of ortho-carbonyl, imino, or azo substituted nitrobenzenes

Authors
Kim, BH Lee, YS Kwon, W Jin, Y Tak, JA Jun, YM Baik, W Lee, BM
Citation
Bh. Kim et al., 2-bromo-2-nitropropane/Zn promoted reductive cyclizations of ortho-carbonyl, imino, or azo substituted nitrobenzenes, HETEROCYCLE, 48(12), 1998, pp. 2581-2592
Citations number
30
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
48
Issue
12
Year of publication
1998
Pages
2581 - 2592
Database
ISI
SICI code
0385-5414(199812)48:12<2581:2PRCOO>2.0.ZU;2-8
Abstract
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 phenylazobenzene s have been converted into 2-aryl-2H-benzotriazoles via reductive cyclizati ons that are widely used as UV absorbers. Synthesis and mechanistic details are discussed.