REARRANGEMENT–CYCLIZATION OF DIALKYL(4-HYDROXYBUT-2-YNYL)METHALLYL- AND DIALKYLCROTYL(4-HYDROXYBUT-2-YNYL)AMMONIUM HALIDES

Authors

  • Э. О. Чухаджян Institute of Organic Chemistry, Scientific–Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, Yerevan 0014
  • А. С. Габриелян Institute of Organic Chemistry, Scientific–Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, Yerevan 0014
  • Эл. О. Чухаджян Institute of Organic Chemistry, Scientific–Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, Yerevan 0014
  • К. Г. Шахатуни Institute of Organic Chemistry, Scientific–Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, Yerevan 0014
  • Г. А. Паносян Molecular Structure Research Center, Scientific–Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, Yerevan 0014

DOI:

https://doi.org/10.1007/6435

Keywords:

N, N-dialkyl-4-(but-1-en-3-yl)-2, 5-dihydrofuran-2-ylamine, N-dialkyl-4-methallyl-2, dialkyl(4-hydroxybut-2-ynyl)methallylammonium chlorides, dialkylcrotyl-(4-hydroxybut-2-ynyl)ammonium bromides, intramolecular cyclization, aqueous-alkali cleavage, Stevens rearrangement

Abstract

It was found that dialkyl(4-hydroxybut-2-ynyl)methallyl- and dialkylcrotyl(4-hydroxybut-2-ynyl)ammonium halides undergo a Stevens rearrangement under the influence of aqueous alkali with transfer of the reaction center in the receiving group and inversion of the migrating group followed by cyclization to amino derivatives of furan.

How to Cite
Chukhajian, E. O. Gabrielyan, A. S.; Chukhajian, El. O.;
Shahkhatuni, K. G.;  Panosyan, H. A. Chem. Heterocycl. Compd. 2009, 45, 1302. [Khim. Geterotsikl. Soedin. 2009, 1622.]

For this article in the English edition see DOI 10.1007/s10593-010-0425-1

 

 

 

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Published

2021-10-01

Issue

No. 11 (2009)

Section

Original Papers