SYNTHESIS OF 2-ARYL-3-METHYLBENZO[<i>g</i>]INDOLES FROM 2-(ARYLETHYNYL)-1,8-BIS(DIMETHYLAMINO)NAPHTHALENES: NEW EXAMPLES OF [1,3]-MIGRATION INVOLVING <i>N</i>-METHYL GROUP

Authors

  • Екатерина А. Филатова Faculty of Chemistry, Southern Federal University
  • Анна В. Гулевская Faculty of Chemistry, Southern Federal University
  • Александр Ф. Пожарский Faculty of Chemistry, Southern Federal University

DOI:

https://doi.org/10.1007/4260

Keywords:

2-alkynyl-1, 8-bis(dimethylamino)naphthalenes, benzo[g]indoles, [1, 3]-migration of methyl group, proton sponge, Sonogashira coupling

Abstract

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.

Author Biographies

Екатерина А. Филатова, Faculty of Chemistry, Southern Federal University

Екатерина Александровна Филатова

кафедра органической химии, доцент

Анна В. Гулевская, Faculty of Chemistry, Southern Federal University

Анна Васильевна Гулевская

кафедра органической химии, профессор

Александр Ф. Пожарский, Faculty of Chemistry, Southern Federal University

Александр Федорович Пожарский

кафедра органической химии, заведующий кафедрой, профессор

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Published

2018-02-17

Issue

Vol. 54 No. 1 (2018)

Section

Original Papers