BASE CATALYZED INTRAMOLECULAR CYCLIZATION OF DIALKYCROTYL(3-ALKENYLPROPYN-2-YL)AMMONIUM SALTS AND AQUEOUS BASE FISSION OF 2,2-DIALKYL-4-METHYL- AND 2,2-DIALKYL-4,6-DIMETHYL-2,6,7,7a-TETRAHYDRO-1H-ISOINDOLIUM BROMIDES

Authors

  • Э. О. Чухаджян Institute of Organic Chemistry, National Academy of Sciences of the Republic of Armenia, Yerevan 375091
  • М. К. Налбандян Institute of Organic Chemistry, National Academy of Sciences of the Republic of Armenia, Yerevan 375091
  • А. Р. Геворкян Institute of Organic Chemistry, National Academy of Sciences of the Republic of Armenia, Yerevan 375091
  • К. Г. Шахатуни Institute of Organic Chemistry, National Academy of Sciences of the Republic of Armenia, Yerevan 375091
  • Г. А. Паносян Molecular Structure Research Center, National Academy of Sciences of the Republic of Armenia, Yerevan 375014

DOI:

https://doi.org/10.1007/7088

Keywords:

2, 2-dialkyl-4-methyl- and -4, 6-dimethyl-2, 6, 7, 7a-tetrahydro-1H-isoindolium bromides, isomeric N, N-dialkylmethyl- and -trimethylbenzylamines, intramolecular cyclization, aqueous base fission, basic catalysis

Abstract

Cyclization of dimethylcrotyl(3-vinyl- or -3-isopropenylpropyn-2-yl)ammonium bromides in the presence of base gave a mixture of the isomeric 2,2-dialkyl-4-methyl- and 2,2-dialkyl-4,6-dimethyl-2,6,7,7a-tetrahydro-1H-isoindolium bromides. Basic fission of the salts obtained at increased temperature gave a mixture of the isomeric N,N- disubstituted di- and trimethylbenzylamines whose structures were confirmed by their IR, 1H NMR, and 13C NMR spectra.

How to Cite
Chukhajian, E. O.; M. K. Nalbandyan, M. K.; Gevorkyan, A. R.; Shakhatuni,  K. G.; Panosyan, G. A.  Chem. Heterocycl. Compd. 2008, 44, 671. [Khim. Geterotsikl. Soedin. 2008, 841.]

For this article in the English edition see DOI 10.1007/s10593-008-0090-9

 

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Published

2022-09-29

Issue

No. 6 (2008)

Section

Original Papers