ISSN:
0021-8383
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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]pyrimidinonesα-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.
Additional Material:
4 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19813230417
