Synthesis of 4-(Hydroxymethyl)dihydroisoindolium Salts and Their Intramolecular Recyclization
- Authors: Chukhadzhyan E.O.1, Gevorgyan H.R.1, Shahkhatuni K.G.1, Chukhadzhyan E.O.1, Ayrapetyan L.V.1, Khachatryan A.A.2
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Affiliations:
- Institute of Organic Chemistry, Scientific Technological Center of Organic and Pharmaceutical Chemistry
- Nalbandyan State Pedagogical Institute
- Issue: Vol 54, No 4 (2018)
- Pages: 517-525
- Section: Review
- URL: https://journals.rcsi.science/1070-4280/article/view/217479
- DOI: https://doi.org/10.1134/S1070428018040012
- ID: 217479
Cite item
Abstract
The review discusses intramolecular cyclization of ammonium salts containing a 4-hydroxybut-2- yn-1-yl group in combination with various π4-fragments, as well as mechanisms of cyclization and intramolecular recyclization of the resulting 4-(hydroxymethyl)dihydroisoindolium salts and their fused analogs. The process is accompanied by neither ring expansion nor contraction, and a pharmacophoric 1,3-dihydrofuran ring is formed instead of dihydroisoindolium fragment. The effects of electronic and structural factors on the intramolecular cyclization and recyclization processes are considered.
About the authors
Em. O. Chukhadzhyan
Institute of Organic Chemistry, Scientific Technological Center of Organic and Pharmaceutical Chemistry
Email: qnarsh@yandex.ru
Armenia, pr. Azatutyan 26, Yerevan, 0014
H. R. Gevorgyan
Institute of Organic Chemistry, Scientific Technological Center of Organic and Pharmaceutical Chemistry
Email: qnarsh@yandex.ru
Armenia, pr. Azatutyan 26, Yerevan, 0014
K. G. Shahkhatuni
Institute of Organic Chemistry, Scientific Technological Center of Organic and Pharmaceutical Chemistry
Author for correspondence.
Email: qnarsh@yandex.ru
Armenia, pr. Azatutyan 26, Yerevan, 0014
El. O. Chukhadzhyan
Institute of Organic Chemistry, Scientific Technological Center of Organic and Pharmaceutical Chemistry
Email: qnarsh@yandex.ru
Armenia, pr. Azatutyan 26, Yerevan, 0014
L. V. Ayrapetyan
Institute of Organic Chemistry, Scientific Technological Center of Organic and Pharmaceutical Chemistry
Email: qnarsh@yandex.ru
Armenia, pr. Azatutyan 26, Yerevan, 0014
A. A. Khachatryan
Nalbandyan State Pedagogical Institute
Email: qnarsh@yandex.ru
Armenia, ul. P. Sevaka 4, Gyumri, 3126
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