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Cyclization of dialkylpropyn-1-yl(allyl)(3-isopropenylpropyn-2-yl)ammonium bromides and water-base cleavage of 2,2-dialkyl-5-methyl-2,6,7,7a-tetrahydro-1h-isoindolium and 2,2-dialkyl-5-methylisoindolinium bromides

✍ Scribed by Emma H. Chukhajian; Martiros K. Nalbandyan; Hasmik R. Gevorkyan; Eliza H. Chukhajian; Henrik A. Panosyan; Armen G. Ayvazyan; Rafael A. Tamazyan

Publisher
Journal of Heterocyclic Chemistry
Year
2008
Tongue
English
Weight
366 KB
Volume
45
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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Dialkylpropyn‐1‐yl(or allyl)(3‐isopropenylpropyn‐2‐yl)ammonium bromides under base‐catalyzed condition instantly undergo intramolecular cyclization. The cyclization of dialkylpropyn‐1‐yl(3‐isopropenylpropyn‐2‐yl)ammonium bromides leads to the formation of 2,2‐dialkyl‐5‐methylisoindolinium salts. In case of allyl analogs, instead of the expected 2,2‐dialkyl‐6‐methyl‐3__a__,4‐dihydroisoindolinium salts their isomeric forms ‐ 2,2‐dialkyl‐5‐methyl‐2,6,7,7__a__‐tetrahydro‐1__H__‐isoindolium bromides are obtained. In alkaline medium they are transform into the dihydroisoindolinium salts, the cleavage of which in two directions ‐ 1,2 and 1,6 leads to the mixture of isomeric dialkyl‐1,4‐dimethyl‐ and 2,4‐dimethylbenzyl‐amines.

Study of the behavior of 2,2‐dialkyl‐5‐methylisoindolinium salts under conditions of water‐base cleavage showed, that only spiro[5‐methylisoindolyn]morpholinium bromide undergoes 1,2‐elimination, forming 5‐methylisoindoline 2‐vinyl ethyl ester.

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