REARRANGEMENT OF 1-ARYLINDOLES TO 5H-DIBENZ[B,F]AZEPINES

Authors
TOKMAKOV GP GRANDBERG II
Citation
Gp. Tokmakov et Ii. Grandberg, REARRANGEMENT OF 1-ARYLINDOLES TO 5H-DIBENZ[B,F]AZEPINES, Tetrahedron, 51(7), 1995, pp. 2091-2098
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
51
Issue
7
Year of publication
1995
Pages
2091 - 2098
Database
ISI
SICI code
0040-4020(1995)51:7<2091:RO1T5>2.0.ZU;2-M
Abstract
An unusual acid-catalyzed rearrangement of 1-arylindoles 1 to 5H-diben z[b,f]azepines 2 has been discovered. It can be used for the preparati on of 2. The influence of the nature and the position of the substitue nts in the initial molecule 1 on the rearrangement is discussed. A pos sible mechanism of the reaction is suggested. A convenient method for preparation of 1-arylindoles 1c-k by means of arylation of 1-unsubstit uted indoles with aryl halides by the Ullmann reaction is described.