1701-95-7

Upstream product

• 5100-23-2 2-isocyanatobenzoyl chloride 
• 79860-15-4 2-[2-(3,3-Dimethyl-ureido)-benzoylamino]-benzoic acid 
• 79860-05-2 2-dimethylammonio-(4H)-3,1-benzoxazine-4-one chloride 
• 118-92-3 anthranilic acid 
• 118-48-9 isatoic anhydride 
• 102081-79-8 diethyl 2,2'-[carbonylbis(azanediyl)]dibenzoate 
• 67-56-1 methanol 

Downstream Products

• 25380-15-8 2-(4-oxo-4H-quinazolin-3-yl)benzoic acid 

Relevant academic research and scientific papers

Radical reactions with 3H-quinazolin-4-ones: Synthesis of deoxyvasicinone, mackinazolinone, luotonin A, rutaecarpine and tryptanthrin

Alkyl, aryl, heteroaryl and acyl radicals have been cyclised onto the 2-position of 3H-quinazolin-4-one. The side chains containing the radical precursors were attached to the nitrogen atom in the 3-position. The cyclisations take place by aromatic homolytic substitution hence retain the aromaticity of the 3H-quinazolin-4-one ring. The highest yields were obtained using hexamethylditin to facilitate cyclisation rather than reduction without cyclisation. The alkaloids deoxyvasicinone 2, mackinazolinone 3, tryptanthrin 4, luotonin A 5 and rutaecarpine 8 were synthesised by radical cyclisation onto 3H-quinazolin-4-one. This journal is The Royal Society of Chemistry.

Structure of the 2-Isocyanatobenzoyl Chloride-Aluminium Chloride (1:2) Complex: Reactions with Some Nucleophiles

The reactions of 2-isocyanatobenzoyl chloride-aluminium chloride (1:2) complex with methanol, aniline, methyl anthranilate, ethyl anthranilate, 2-aminobenzophenone, 2-amino-5-chlorobenzophenone have been studied.Based on the products obtained in these reactions, the 1:2 complex has been shown to be a mixture of acyclic and cyclic structures (4) and (5) respectively.This is in accordance with the observations recorded in IR studies.

HETEROCYCLIZATION WITH IMINIUM CHLORIDES, II. SYNTHESIS OF 4H--BENZOXAZINE-4-ONES AND QUINAZOLINONES

Reactions between methyl anthranilate and a variety of PI salts afforded 2-ammonio-4H--benzoxazine-4-one chlorides which were subjected to nucleophilic reactions.With primary amines, 2-ureidoanthraniloyl amides were obtained, which were smoothly cyclized in boiling acetic anhydride or dimethylformamide to give 1H,3H-quinazoline-2,4-diones.