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• 5202-85-7 2-Amino-5-chlorobenzamide 
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• 4743-17-3 5-Chloroisatoic anhydride 
• 89-97-4 2-CHLOROBENZYLAMINE 
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• 89-98-5 2-chloro-benzaldehyde 

Relevant academic research and scientific papers

A new efficient method for the three-component synthesis of 4(3H)-Quinazolinones

4(3H)-Quinazolinones were efficiently synthesised by the three component cyclisation-oxidation of isatoic anhydride, ammonium acetate and aromatic aldehydes in the presence of ceric ammonium nitrate in ethanol. The Japan Institute of Heterocyclic Chemistry.

Electro-oxidative cyclization: Access to quinazolinones: Via K2S2O8without transition metal catalyst and base

A K2S2O8-promoted oxidative tandem cyclization of primary alcohols with 2-aminobenzamides to synthesize quinazolinones was successfully achieved under undivided electrolytic conditions without a transition metal and base. The key feature of this protocol is the utilization of K2S2O8 as an inexpensive and easy-to-handle radical surrogate that can effectively promote the reaction via a simple procedure, leading to the formation of nitrogen heterocycles via direct oxidative cyclization at room temperature in a one-pot procedure under constant current. Owing to the use of continuous-flow electrochemical setups, this green, mild and practical electrosynthesis features high efficiency and excellent functional group tolerance and is easy to scale up.

Copper-Catalyzed Intramolecular α-C-H Amination via Ring-Opening Cyclization Strategy to Quinazolin-4-ones: Development and Application in Rutaecarpine Synthesis

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.

Iron(III) Chloride-Catalyzed Decarboxylative-Deaminative Functionalization of Phenylglycine: A Tandem Synthesis of Quinazolinones and Benzimidazoles

The first iron(III) chloride-catalyzed decarboxylative-deaminative functionalization of phenylglycine with o-substituted nitroarenes was achieved for the synthesis of 4(3H)-quinazolinones and benzimidazoles. The reaction of 2-nitrobenzonitrile/2-nitro-N,N-diphenylamine with phenylglycine at 120 C in the presence of potassium carbonate as a base in toluene generated the products in 45-87% yields. Various functional groups like nitro, fluoride, chloride and trifluoromethyl were well tolerated under the present reaction conditions. In this tandem approach, involvement of transfer hydrogenation of the nitro functionality with in situ generated ammonia, imination, nitrile hydration to amide and oxidative cyclization sequences have been established. The process avoids the use of an external hydrogen source, costly catalysts as well as the isolation of amine and amide intermediates.

A novel one-pot synthesis of 2-aryl-4(3H)-quinazolinones using room temperature ionic liquid as reaction medium as well as promoter

An efficient one-pot synthesis of 2-aryl-4(3H)-quinazolinones from 2-amino benzamides and substituted benzoyl chlorides in a room temperature ionic liquid is described. Compared with the classical reaction conditions, this new synthetic method has the advantages of recyclability of ionic liquid, very good to excellent yields (78-92%), the absence of hazardous and expensive catalysts, and easy workup procedures giving rise to a process with minimum waste.