The Dimerization of 2-Amino-5-nitrobenzonitrile

Abstract

Vol. 82 2-Amino-5-nitrobenzonitrile dimerizes readily a t 180' in alcoholic ammonia to give 2-(2-amino-5-ni trophenyl)-4-amino-6-nitroquinazoline ( V I 1 1. The structure of VI1 was rigorously confirmed by conversion to 2-(3-nitrophenyl)-6-nitro-4(3H)-quinazolone ( I X ) and t o 2-(2-amino-5-nitrophenyl)-6-nitro-4(3H)-quinazolone ( X I I ) , both of which were then synthesized independently. I t was found t h a t aromatic o-aminonitriles undergo intermolecular condensations with aromatic nitriles in basic media t o give 2-aryl-4-aminoquinazolines in good yield, and t h a t this reaction constitutes a general method for the synthesis of fused 4-aminopyrimidine heterocycles. The mechanisms of these condensation and dimerization reactions are discussed.

Synthesis of Benzotriazine and Aryltriazene Derivatives Starting from 2‐Azidobenzonitrile Derivatives

“…94-95°C (ref. [46] [33] Bromine (6.5 mL, 127.1 mmol) was added dropwise to a solution of 2-aminobenzonitrile (6a; 5.0 g, 42.4 mmol) in acetic acid (100 mL). The reaction mixture was stirred at room temperature overnight and the white precipitate was collected by filtration.…”

Quinazolin-4-one derivatives lacking toxicity-producing attributes as glucokinase activators: design, synthesis, molecular docking, and in-silico ADMET prediction

“…The reaction of anthranilic acid (1) with acetic anhydride/ propionic anhydride yielded 2-methyl-4H-3,1-benzoxazin-4-one (2)/ 2-ethyl-4H-3,1-benzoxazin-4-one (11) respectively and with benzoyl chloride yielded 2-phenyl-4H-3,1-benzoxazin-4-one (20) [21,22]. The reaction of 2-substituted benzoxazinone (2,11,20) (12) and ethyl-[2-(4-oxo-2-phenylquinazolin-3(4H)-yl)-1,3-thiazol-4-yl]acetate (21), respectively. In this reaction, nitrogen nucleophile readily attacks the reactive 4th position of benzoxazinone, followed by ring opening and then closing to generate quinazolinones.…”

“…In this reaction, nitrogen nucleophile readily attacks the reactive 4th position of benzoxazinone, followed by ring opening and then closing to generate quinazolinones. The reaction of different aromatic primary amines with 2-substituted quinazolinone acetate (3,12,21) in dry pyridine yielded the corresponding 2-substituted quinazoline-4-one amide derivatives (4-10, 13-19, 22-28) by ammonolysis of esters as portrayed in Scheme 1.…”

Synthesis of 3H‐Quinazolin‐4‐ones and 4H‐3,1‐Benzoxazin‐4‐ones via Benzylic Oxidation and Oxidative Dehydrogenation using Potassium Iodide‐tert‐Butyl Hydroperoxide

“…[10d] Conventional methods for the preparation of 3H-quinazolin-4-ones employ the coupling of 2-aminobenzoic acid or its derivatives with acyl chloride or carboxylic acid anhydride to give benzoxazinone which on subsequent addition to an amine yields the desired product. [11] Other synthetic routes include the microwave-assisted three-component methodology from anthranilic acids, [12] solvent-free synthesis from isatoic anhydride and orthoester with primary amine employing silica-sulphuric acid (SSA) [13a] and a solidphase traceless synthesis.…”