CYCLIZATION OF DIALKYL(3-PHENYLPROPEN-2-YL)(3-PHENYLPROPYN-2-YL)AMMONIUM BROMIDES BY THE ACTION OF AN AQUEOUS ALKALI SOLUTION. AQUEOUS-ALKALINE CLEAVAGE OF THE CYCLIZATION PRODUCTS – <i>N</i>,<i>N</i>-DIALKYL-4(9)-PHENYL-3a,4-DIHYDROBENZO[<i>f</i>]ISOINDOLINIUM BROMIDES

Authors

  • Э. О. Чухаджян Scientific Technological Center of Organic and Pharmaceutical Chemistry of National Academy of Sciences, Republic of Armenia
  • Л. В. Айрапетян Scientific Technological Center of Organic and Pharmaceutical Chemistry of National Academy of Sciences, Republic of Armenia
  • Эл. О. Чухаджян Scientific Technological Center of Organic and Pharmaceutical Chemistry of National Academy of Sciences, Republic of Armenia
  • Г. А. Паносян Scientific Technological Center of Organic and Pharmaceutical Chemistry of National Academy of Sciences, Republic of Armenia

DOI:

https://doi.org/10.1007/931

Keywords:

(dialkylaminomethyl)naphthalenes, dialkyl(3-phenylpropen-2-yl)(3-phenylpropyn-2-yl)ammonium bromides, isoindolinium salts, aqueous-alkaline cleavage, intramolecular cyclization

Abstract

When heated in an alkaline aqueous medium, dialkyl(3-phenylpropen-2-yl)(3-phenylpropyn-2-yl)- ammonium bromides undergo intramolecular cyclization, forming N,N-dialkyl-4(9)-phenyl-3a,4-dihydrobenzo[f]isoindolinium bromides. The cyclization products undergo aqueous-alkaline cleavage at the C(1)–N(2) or N(2)–C(3) bond, which leads to a mixture of 2-(dialkylaminomethyl)-3-methyl- and 3-(dialkylaminomethyl)-2-methyl-1-phenylnaphthalenes. However, only the C(1)–N(2) bond cleavage product is formed in the case of 2,2-pentamethylene-9-phenyl-3a,4-dihydrobenzo[f]isoindolinium bromide.

Authors: E. O. Chukhajian, L. V. Ayrapetyan, El. O. Chukhajian, and H. A. Panosyan

English Translation in Chemistry of Heterocyclic Compounds, 2012, 48 (9), pp 1314-1320

http://link.springer.com/article/10.1007/s10593-012-1138-4

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Published

2013-09-03

Issue

No. 9 (2012)

Section

Original Papers