234444-48-5Relevant articles and documents
NaNO2/I2 as an alternative reagent for the synthesis of 1,2,3-benzotriazin-4(3H)-ones from 2-aminobenzamides
Barak, Dinesh S.,Mukhopadhyay, Sushobhan,Dahatonde, Dipak J.,Batra, Sanjay
supporting information, p. 248 - 251 (2019/01/04)
An efficient transformation of 2-aminobenzamides to 1,2,3-benzotriazin-4(3H)-ones in the presence of sodium nitrite (NaNO2) and Iodine (I2) is described. The reaction is proposed to proceed via formation of nitrosyl halide that induces nitrosylation of the amino group of 2-aminobenzamide leading to diazotization followed by intramolecular cyclization.
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.
