Synthesis of 4-(Hydroxymethyl)dihydroisoindolium Salts and Their Intramolecular Recyclization


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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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