STUDY OF THE BEHAVIOR OF <i>p</i>-BIS{3-[N,N-DIALKYL-N-(4-HYDROXYBUT-2-YNYL)AMMONIO]PROP-2-YNYL}BENZENE DICHLORIDES IN RELATION TO AQUEOUS ALKALI. DOUBLE INTRAMOLECULAR RECYCLIZATION OF BENZO[5,6;5',6'-<i>a</i>,<i>c</i>]DI(2,2-DIALKYL-4-HYDROXYMETHYL)ISOINDOLINIUM DICHLORIDES

Authors

  • Э. О. Чухаджян Institute of Organic Chemistry, National Academy of Sciences of Armenia, Erevan 375091
  • А. Р. Геворкян Institute of Organic Chemistry, National Academy of Sciences of Armenia, Erevan 375091
  • А. А. Хачатрян Institute of Organic Chemistry, National Academy of Sciences of Armenia, Erevan 375091
  • Эл. О. Чухаджян Institute of Organic Chemistry, National Academy of Sciences of Armenia, Erevan 375091
  • Г. А. Паносян Center for the Investigation of Molecular Structures, National Academy of Sciences of Armenia, Erevan 375014

DOI:

https://doi.org/10.1007/7811

Keywords:

benzo[5, 6, 5', 6'-a, c]di(2, 2-dialkyl-4-hydroxymethyl)isoindolinium salts, p-bis{3-[N, N-dialkyl-N-(4-hydroxybut-2-ynyl)ammonio]prop-2-ynyl}benzene dichlorides, dialkyl(6-dialkylaminomethyl-7, 9, 10, 12-tetrahydro-8, 11-dioxadicyclopenta[c, g]phenanthren-1-ylmethyl)amines, base catalysis, double intramolecular cyclization, intramolecular recyclization

Abstract

p-Bis{3-[N,N-dialkyl-N-(4-hydroxybut-2-ynyl)ammonio]prop-2-ynyl}benzene dichloride  in the presence of  catalytic amounts of aqueous alkali is subject to a double intramolecular cyclization forming benzo[5,6;5',6'-a,]di(2,2-dialkyl-4-hydroxymethyl)isoindolinium dichloride in 40-42%  yield. Simultaneously an intramolecular recyclization takes place with the formation  of  dialkyl(6-dialkylaminomethyl-7,9,10,12-tetrahydro-8,11-dioxadicyclopenta[c,]phenanthren-1-ylmethyl)amines in 7-9% yield. The same compounds are obtained  in 70-72% yield by the recyclization of  benzo-[5,6;5',6'-a,]di(2,2-dialkyl-4-hydroxymethyl)isoindolinium dichlorides under conditions of aqueous alkaline degradation.

How to Cite
Chukhadzhyan, E. O.; Gevorkyan, A. R.; Khachatryan, A. A.; Chukhadzhyan, El. O.; Panosyan, G. A.  Chem. Heterocycl. Compd. 2006, 42, 1151. [Khim. Geterotsikl. Soedin. 2006, 1329.]

For this article in the English edition see DOI 10.1007/s10593-006-0219-7


Published

2023-05-18

Issue

No. 9 (2006)

Section

Original Papers