221539-37-3Relevant academic research and scientific papers
An efficient one pot synthesis of 2-amino quinazolin-4(3H)-one derivative via MCR strategy
Narayana Murthy,Nikumbh, Satish P.,Praveen Kumar,Vaikunta Rao,Raghunadh, Akula
, p. 5767 - 5770 (2015)
A novel multi-component reaction strategy was developed for the construction of important building blocks, 2-amino 3-substituted quinazolinone derivatives from isatoic anhydride and amine with electrophilic cyanating compound, N-cyano-4-methyl-N-phenylbenzenesulfonamide (NCTS). The quinazolinone synthesis proceeds via a sequential series of reactions such as nucleophilic attack of the amine group on the carbonyl group of isatoic anhydride followed ring opening and subsequent decarboxylation, nucleophilic attack of amine to nitrile, followed by heterocyclization.
Copper-Catalyzed Intramolecular α-C-H Amination via Ring-Opening Cyclization Strategy to Quinazolin-4-ones: Development and Application in Rutaecarpine Synthesis
Biswal, Sonali,Chada, Harika,Patel, Srilaxmi M.,Sharada, Duddu S.,Sharma, Sonika
, p. 3160 - 3170 (2019/08/07)
A copper-catalyzed intramolecular α-C-H amination has been developed for the synthesis of quinazolin-4(3 H)-one derivatives from commercially available isatoic anhydride and primary and secondary benzylamines via ring-opening cyclization (ROC). This method shows good functional group tolerance and allows access to a range of 2-aryl, 2-alkyl, and spiroquinazolinone derivatives. However, 2-methylquinazolin-4(3 H)-one was synthesized from 2-amino- N -isopropylbenzamide by C-C bond cleavage, and N -benzyl-2-(methylamino)benzamide afforded 1-methyl-2-phenylquinazolin-4(1 H)-one along with 2-phenylquinazolin-4(3 H)-one by N-C bond cleavage for aromatization. It is the first general method to construct the potentially useful 2-methylquinazolin-4(3 H)-one by copper-catalyzed intramolecular C-H amination. Also this ROC strategy has been successfully applied to the synthesis of quinazolinone alkaloid rutaecarpine.
