Oxidative free radical reactions between 2-amino-1,4-naphthoquinones and carbonyl compounds

Authors
Wu, YL Chuang, CP Lin, PY
Citation
Yl. Wu et al., Oxidative free radical reactions between 2-amino-1,4-naphthoquinones and carbonyl compounds, TETRAHEDRON, 57(26), 2001, pp. 5543-5549
Citations number
35
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
26
Year of publication
2001
Pages
5543 - 5549
Database
ISI
SICI code
0040-4020(20010625)57:26<5543:OFRRB2>2.0.ZU;2-Q
Abstract
The manganese(m) initiated oxidative free radical reaction provides a novel method for the synthesis of benzo[f]indole-4,9-diones from 2-amino-1,4-nap hthoquinones and carbonyl compounds. The regioselectivity of this reaction was also studied with unsymmetrical ketones from which both isomeric indole s 10 and 11 were formed. With alpha -halo, alpha -phenoxy and alpha -methan esulfonyl ketones, in most cases, this reaction gave high regioselectivity. With 2-alkyl substituted-1,3-dione 14, indole 11 was obtained as the only product. (C) 2001 Elsevier Science Ltd. All rights reserved.