234444-48-5

Upstream product

• 31162-13-7 2-azidobenzoic acid 
• 944838-62-4 2-(5-aminomethyl-1-tetrazolyl)benzoic acid 
• 944838-60-2 2-(5-chloromethyl-1-tetrazolyl)benzoic acid 
• 6011-14-9 2-aminoacetonitrile hydrochloride 
• 234444-50-9 4H-tetrazolo[1,5-a][1,4]benzodiazepin-6-one 
• 118-48-9 isatoic anhydride 
• 151-63-3 cyanomethylamine sulfate 
• 234444-49-6 N-cyanomethyl-2-azidobenzamide 

Downstream Products

• 76109-80-3 2-(4-oxobenzo[d][1,2,3]triazin-3(4H)-yl)acetonitrile 
• 234444-49-6 N-cyanomethyl-2-azidobenzamide 
• 350494-60-9 2-(benzylthio)-4-oxo-3(4H)quinazolineacetonitrile 

Relevant academic research and scientific papers

NaNO2/I2 as an alternative reagent for the synthesis of 1,2,3-benzotriazin-4(3H)-ones from 2-aminobenzamides

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 novel approach to the synthesis of 4H-tetrazolo[1,5-a][1,4]benzodiazepin- 6-ones from 1,2,3-benzotriazin-4-(3H)-ones

Two novel routes have been developed for the synthesis of 4H-tetrazolo[1,5-a][1,4]benzodiazepin-6-ones 6a-b from 3-substituted 1,2,3-benzotriazin-4-(3H)-ones 2a-b and 9.

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

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.

Synthesis of tetrazolo[1,5-a][1,4]benzodiazepin-6-ones via intramolecular azide cycloadditions onto the cyano group

Intramolecular azide cycloadditions onto the cyano group are described as a synthetic tool for a number of tetrazolo[1,5-a][1,4]benzodiazepin-6- ones (3).