From benzil arylimines to 2H-benzo-1,4-thiazines, benzothiazoles or indoles

Authors
Charrier, JD Landreau, C Deniaud, D Reliquet, F Reliquet, A Meslin, JC
Citation
Jd. Charrier et al., From benzil arylimines to 2H-benzo-1,4-thiazines, benzothiazoles or indoles, TETRAHEDRON, 57(19), 2001, pp. 4195-4202
Citations number
31
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
19
Year of publication
2001
Pages
4195 - 4202
Database
ISI
SICI code
0040-4020(20010507)57:19<4195:FBAT2B>2.0.ZU;2-L
Abstract
A series of benzil monoarylimines (1) was treated with phosphorus pentasulf ide in refluxing toluene or xylene. Thionation of 1 occurred readily to aff ord either 2H-benzo-1,4-thiazines (2) or indoles (4) via annulation reactio ns, depending strongly on the nature of the meta substituent of the arylami no group. Mechanisms for these rearrangements were proposed. Furthermore, s ubsequent oxidation of 2 provided benzothiazoles (3). AU compounds were ful ly characterized by IR, MS, C-13 and H-1 NMR. (C) 2001 Elsevier Science Ltd . All rights reserved.