Synthesis of 2,3‐dihydro‐3‐hydroxy‐2‐(pyrrol‐1‐ylmethyl)‐1H‐isoindol‐1‐one. An intermediate for the synthesis of tetracyclic systems
Identifieur interne : 001228 ( France/Analysis ); précédent : 001227; suivant : 001229Synthesis of 2,3‐dihydro‐3‐hydroxy‐2‐(pyrrol‐1‐ylmethyl)‐1H‐isoindol‐1‐one. An intermediate for the synthesis of tetracyclic systems
Auteurs : Anna Korenova [Slovaquie] ; Pierre Netchitailo [France] ; Bernard Decroix [France]Source :
- Journal of Heterocyclic Chemistry [ 0022-152X ] ; 1998-01.
Abstract
N‐Chloromethylphthalimide 1 and the potassium salt of pyrrole gave N‐(pyrrol‐1‐ylmethyl)pbthalimide 2. Reduction of 2 led to the hydroxyisoindolone 3. This hydroxylactam cyclized under acidic conditions to lead to a pyrroloimidazoloisoindolone 4 via an acyliminium ion. Transformation of 3 with acetic acid derivatives provided 5, 7 and 9 which gave by intramolecular cyclization, tetracyclic compounds 6, 10 and 11.
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DOI: 10.1002/jhet.5570350102
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<front><div type="abstract">N‐Chloromethylphthalimide 1 and the potassium salt of pyrrole gave N‐(pyrrol‐1‐ylmethyl)pbthalimide 2. Reduction of 2 led to the hydroxyisoindolone 3. This hydroxylactam cyclized under acidic conditions to lead to a pyrroloimidazoloisoindolone 4 via an acyliminium ion. Transformation of 3 with acetic acid derivatives provided 5, 7 and 9 which gave by intramolecular cyclization, tetracyclic compounds 6, 10 and 11.</div>
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