27895-78-9

Upstream product

• 109-73-9 N-butylamine 
• 552-89-6 2-nitro-benzaldehyde 

Downstream Products

• 132784-75-9 1-nitro-2-(2-chloro-2-nitroethenyl)benzene 
• 195611-42-8 diethyl 1-(N-butylamino)-2-nitrobenzylphosphonate 
• 195611-38-2 1-(N-butylamino)-2-nitrobenzylphosphonic acid 
• 1353055-51-2 N-(2-nitrobenzylidene)-1H-imidazol-2-amine 
• 67796-16-1 2-phenyl-3-n-butylquinazoline-4(3H)-one 
• 85094-65-1 3-butyl-2-(4-methoxy-phenyl)-3H-quinazolin-4-one 
• 1341123-77-0 3-butyl-2-(4-chlorophenyl)quinazolin-4(3H)-one 

Relevant academic research and scientific papers

Facile synthesis of 4-substituted 1,2,4,5-tetrahydro-1,4-benzodiazepin-3-ones by reductive cyclization of 2-chloro-N-(2-nitrobenzyl)acetamides

A facile and efficient method was developed for the synthesis of 1,2,4,5-tetrahydro-1,4-benzodiazepine-3-ones from 2-chloro-N-(2-nitrobenzyl)acetamides through a reductive cyclization using iron-ammonium chloride in ethanol–water in good yields. This method provides a simple approach to these benzodiazepine-3-ones which are of high value in the field of medicinal chemistry research.

A Biphilic Phosphetane Catalyzes N-N Bond-Forming Cadogan Heterocyclization via PIII/PV = O Redox Cycling

A small-ring phosphacycle, 1,2,2,3,4,4-hexamethylphosphetane, is found to catalyze deoxygenative N-N bond-forming Cadogan heterocyclization of o-nitrobenzaldimines, o-nitroazobenzenes, and related substrates in the presence of hydrosilane terminal reductant. The reaction provides a chemoselective catalytic synthesis of 2H-indazoles, 2H-benzotriazoles, and related fused heterocyclic systems with good functional group compatibility. On the basis of both stoichiometric and catalytic mechanistic experiments, the reaction is proposed to proceed via catalytic PIII/PV = O cycling, where DFT modeling suggests a turnover-limiting (3+1) cheletropic addition between the phosphetane catalyst and nitroarene substrate. Strain/distortion analysis of the (3+1) transition structure highlights the controlling role of frontier orbital effects underpinning the catalytic performance of the phosphetane.

Quinazolinones, Quinazolinthiones, and Quinazolinimines as Nitric Oxide Synthase Inhibitors: Synthetic Study and Biological Evaluation

The synthesis of different compounds with a quinazolinone, quinazolinthione, or quinazolinimine skeleton and their in vitro biological evaluation as inhibitors of inducible and neuronal nitric oxide synthase (iNOS and nNOS) isoforms are described. These d

NHC-Catalyzed Benzylic Csp3–H Bond Activation of Alkylarenes and N-Benzylamines for the Synthesis of 3H-Quinazolin-4-ones: Experimental and Theoretical Study

An N-heterocyclic carbene catalyzed benzylic Csp3–H bond activation of alkylarenes and N-benzylamines under metal-free conditions was developed. This organocatalyzed oxidative transformation afforded the corresponding carbonyl derivatives in good to excellent yields. A variety of alkylarenes and N-benzylamines were tolerated under the optimized reaction conditions. The established method was further extended to the synthesis of biologically important 3H-quinazolin-4-ones in good yields. For example, NPS 53574, a potent calcium receptor antagonist, was successfully synthesized by using this oxidative protocol. DFT studies show that the benzylic C–H bond activation proceeds through the nucleophilic attack of the free carbene on the benzylic carbon atom.

Regioselective synthesis of 2 H-indazoles using a mild, one-pot condensation-cadogan reductive cyclization

An operationally simple and efficient one-pot synthesis of 2H-indazoles from commercially available reagents is reported. Ortho-imino-nitrobenzene substrates, generated via condensation, undergo reductive cyclization promoted by tri-n-butylphosophine to afford substituted 2H-indazoles under mild reaction conditions. A variety of electronically diverse ortho-nitrobenzaldehydes and anilines were examined. To further extend the scope of the transformation, aliphatic amines were also employed to form N2-alkyl indazoles selectively under the optimized reaction conditions.

The cleavage of 1-amino-2'-nitrobenzylphosphonates in a basic medium. Formation of the 3-amino-2,1-benzisoxazole derivatives

Treatment of 1-amino-2'-nitrobenzylphosphonic acids with aqueous sodium hydroxide caused a C-P bond cleavage, with formation of 3-amino-2,1-benzisoxazole derivatives (3). The leaving phosphorus moiety was identified here as phosphoric acid. In the case of basic hydrolysis of corresponding esters, new cyclic phosphorus compounds (derivatives of benzoxazaphosphorin-3,1,2 P(v)-one-2) were obtained. The cyclic products were formed as a result of the subsequent reaction of anthranil derivatives with leaving phosphorus fragment, presumably metaphosphate, These benzoxazaphosphorins (cormpounds 4) were converted by means of aqueous hydrochloric acid to 3-amino-2,1-benzisoxazole derivatives.