Chukhajian, Emma H.;
Nalbandyan, Martiros K.;
Gevorkyan, Hasmik R.;
Chukhajian, Eliza H.;
Panosyan, Henrik A.;
Ayvazyan, Armen G.;
Tamazyan, Rafael A.
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
You can manage bookmarks using lists, please log in to your user account for this.
Media type:
E-Article
Title:
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
Contributor:
Chukhajian, Emma H.;
Nalbandyan, Martiros K.;
Gevorkyan, Hasmik R.;
Chukhajian, Eliza H.;
Panosyan, Henrik A.;
Ayvazyan, Armen G.;
Tamazyan, Rafael A.
imprint:
Wiley, 2008
Published in:Journal of Heterocyclic Chemistry
Language:
English
DOI:
10.1002/jhet.5570450309
ISSN:
0022-152X;
1943-5193
Origination:
Footnote:
Description:
<jats:title>Abstract</jats:title><jats:p><jats:chem-struct-wrap><jats:chem-struct><jats:graphic xmlns:xlink="http://www.w3.org/1999/xlink" mimetype="image/gif" position="anchor" specific-use="enlarged-web-image" xlink:href="graphic/must001.gif"><jats:alt-text>magnified image</jats:alt-text></jats:graphic></jats:chem-struct></jats:chem-struct-wrap></jats:p><jats:p>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<jats:italic>a</jats:italic>,4‐dihydroisoindolinium salts their isomeric forms ‐ 2,2‐dialkyl‐5‐methyl‐2,6,7,7<jats:italic>a</jats:italic>‐tetrahydro‐1<jats:italic>H</jats:italic>‐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.</jats:p><jats:p>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.</jats:p>