Synthese von Pyrrolo[1,2-a]chinazolinonen, Indolo[1,2-a]chinazolinonen, Pyrrolo[1,2-a]thieno[3,2-e]pyrimidinonen, Benzothieno[3,2-e]-pyrrolo[1,2-a]pyrimidinonen und 6H-Cyclohepta[4,5]thieno-[3,2-e]pyrrolo[1,2-a]pyrimidinonen

✍ Scribed by Dr. M. Süsse; Prof. Dr. S. Johne

• Book ID: 105352336
• Publisher: John Wiley and Sons
• Year: 1981
• Tongue: English
• Weight: 362 KB
• Volume: 323
• Category: Article
• ISSN: 1615-4150
• DOI: 10.1002/prac.19813230417

✦ Synopsis

A Synthesis of Pyrrolo[1,2‐a]quinazolinones, Indolo[1,2‐a]‐quinazolinones, Pyrrolo[1,2‐a]thieno[3,2‐e]pyrimidinones, Benzothieno[3,2‐e]pyrrolo[1,2‐a]pyrimidinones and 6H‐Cyclohepta[4,5]‐thieno[3,2‐e]pyrrolo[1,2‐a]pyrimidinones

α‐Cyano‐γ‐halo‐crotonnitriles (1) synthesized (e.g. via Knoevenagel reaction and by subsequent halogenation) react with primary arylamines (2) to substituted 1‐aryl‐2‐amino‐3‐cyano‐pyrroles (3). We found that the reaction yields pyrrolo[1,2‐a]quinazolin‐5‐ones (6) in a one‐pot procedure if anthranilic esters (4) and compounds of the general formula 5 are used. The analogous treatment with 2‐amino‐3‐ethoxy‐carbonyl‐thiophene derivatives (8) leads to pyrrolo[1,2‐a]thieno‐[3,2‐e]pyrimidin‐5‐ones, benzothieno[3,2‐e]pyrrolo[1,2‐a]pyrimidinones and 6H‐Cyclohepta[4,5]‐thieno[3,2‐e]pyrrolo[1,2‐a]pyrimidinones as thiadiazastereoid analogs 9.

This reaction is suitable for the synthesis of various heterocyclic ring systems.