Synthesis of 2,3-dihydro-3-hydroxy-2-(pyrrol-1-ylmethyl)-1H-isoindol-1-one. An intermediate for the synthesis of tetracyclic systems

✍ Scribed by Anna Korenova; Pierre Netchitailo; Bernard Decroix

• Publisher: Journal of Heterocyclic Chemistry
• Year: 1998
• Tongue: English
• Weight: 284 KB
• Volume: 35
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570350102

✦ Synopsis

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.