Synthesis of 2-aryl-3-methylbenzo[g]indoles from 2-naphthalenes: new examples of [1,3]-migration involving N-methyl group

The Sonogashira coupling of 1,8-bis(dimethylamino)-2-iodonaphthalene with 2-nitro-, 4-nitro-, 4-(trifluoromethyl)-, and 4-methoxyphenylacetylenes was used to obtain new 2-(arylethynyl)-1,8-bis(dimethylamino)naphthalenes. Three of the four alkynes, except for the o-nitrophenyl derivative, were isomer...

Full description

Saved in:
Bibliographic Details
Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2018-01, Vol.54 (1), p.38
Main Authors: Filatova, Ekaterina A, Gulevskaya, Anna V, Pozharskii, Alexander F
Format: Article
Language:English
Subjects:
Acetylene
Palladium
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The Sonogashira coupling of 1,8-bis(dimethylamino)-2-iodonaphthalene with 2-nitro-, 4-nitro-, 4-(trifluoromethyl)-, and 4-methoxyphenylacetylenes was used to obtain new 2-(arylethynyl)-1,8-bis(dimethylamino)naphthalenes. Three of the four alkynes, except for the o-nitrophenyl derivative, were isomerized in the presence of palladium and porcelain catalysis to the corresponding 2-aryl-9-(dimethylamino)-1,3-dimethyl-1H-benzo[g]indoles.
ISSN:0009-3122
DOI:10.1007/s10593-018-2227-9