350494-60-9Relevant academic research and scientific papers
A new dimerization reaction producing 2-amino-9-oxopyrrolo-[2,1-b]quinazoline-1-carbonitriles and analogous pyrrolo-[1,2-a]thieno[3,2-d]pyrimidinecarbonitriles
Guetschow,Powers
, p. 419 - 424 (2007/10/03)
A series of 2-alkylthio-4-oxo-3-quinazolineacetonitriles 4 and 2-alkylthio-4-oxothieno[3,2-d]pyrimidine-3-acetonitriles 8 was prepared. Upon treatment with sodium hydride, compounds 4 and 8 react to give 2-amino-4,9-dihydro-9-oxopyrrolo[2,1-b]quinazoline-1-carbonitriles 9 and 6-amino-4,9-dihydro-9-oxopyrrolo[1,2-a]thieno [3,2-d]pyrimidine-7-carbonitriles 10, respectively. The transformation of compounds 4 and 8 to the tricyclic aminonitriles 9 and 10 involves a dimerization step followed by a pyrrole cyclization. The tert-butyl ester derivatives 4d and 8d upon treatment with sodium hydride underwent a Thorpe-Ziegler cyclization to provide enaminoesters of fused 1,3-thiazines (16 and 17, respectively) as major products.
