Synthesis of 4-(Hydroxymethyl)dihydroisoindolium Salts and Their Intramolecular Recyclization |
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| Authors: | Em. O. Chukhadzhyan H. R. Gevorgyan K. G. Shahkhatuni El. O. Chukhadzhyan L. V. Ayrapetyan A. A. Khachatryan |
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| Affiliation: | 1.Institute of Organic Chemistry, Scientific Technological Center of Organic and Pharmaceutical Chemistry,National Academy of Sciences of Armenia,Yerevan,Armenia;2.Nalbandyan State Pedagogical Institute,Gyumri,Armenia |
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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. |
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