19376-65-9

Upstream product

• 64-17-5 ethanol 
• 885674-31-7 2-benzyl-3,4-diphenyl-[1,2,4]oxadiazolin-5-one 
• 141-52-6 sodium ethanolate 
• 538-51-2 benzylidene phenylamine 
• 98-09-9 benzenesulfonyl chloride 
• 93-98-1 N-phenyl benzoyl amide 
• 88333-03-3 Benzyl isocyanide 
• 622-37-7 Phenyl azide 
• 98-80-6 phenylboronic acid 
• 100-52-7 benzaldehyde 
• 62-53-3 aniline 
• 100-46-9 benzylamine 
• 98-88-4 benzoyl chloride 
• 46721-83-9 N-(chloro(phenyl)methylene)(phenyl)methanamine 

Downstream Products

• 31730-65-1 2,4-diphenylquinazoline 
• 739-88-8 1-benzyl-2-phenyl-1H-1,3-benzimidazole 
• 1609460-70-9 1-benzyl-6-ethoxy-2-phenyl-1H-benzo[d]imidazole 
• 1609460-33-4 N-benzyl-N′-(4-bromophenyl)benzimidamide 
• 1229609-99-7 6-bromo-2,4-diphenylquinazoline 
• 56844-88-3 N'-benzyl-N-methyl-N-phenyl-benzamidine 

Relevant academic research and scientific papers

Copper-Catalyzed Three-Component Cascade Reaction of Benzaldehyde with Benzylamine and Hydroxylamine or Aniline: Synthesis of 1,2,4-Oxadiazoles and Quinazolines

The analogous three-component synthesis strategy for substituted 1,2,4-oxadiazole and quinazoline derivatives from readily available benzaldehyde, benzylamine and hydroxylamine or aniline has been developed. Both the cascade reaction sequences involves nucleophilic addition of C?N bond, introduction a halogen donor, nucleophilic substitution and Cu(II)-catalyzed aerobic oxidation. This synthesis methodology demonstrated good yields, broad substrate scope and oxygen as a green oxidant. Thus, this synthesis protocol provides strategies for the construction of substituted 1,2,4-oxadiazole and quinazolines from readily and simple starting materials. (Figure presented.).

Silver(II) oxide-mediated synthesis of 2,4-diarylquinazolines

A single-pot procedure for the synthesis of 2,4-diarylquinazolines is described which involves a silver oxide-mediated C–H activation/C–N bond formation process. The generality of this method with respect to substituent effects is presented along with studies leading to process optimization. Mechanistic investigations provide support for the involvement of radical intermediates in the reaction process.

Tandem Coupling of Azide with Isonitrile and Boronic Acid: Facile Access to Functionalized Amidines

Amidine is a notable nitrogen-containing structural motif found in bioactive natural products and pharmaceuticals. Herein, a novel rhodium(I)-catalyzed tandem reaction of readily accessible azides with isonitriles and boronic acids via a carbodiimide intermediate is achieved. This protocol offers an alternative approach toward N-sulfonyl-, N-acyl-, and N- phosphoryl-functionalized, as well as general N-aryl and N-alkyl amidines with broad substrate scope. In addition, functionalized guanidines can also been synthesized when amines are used instead. The accomplishment of estrone-derived amidine and glibenclamide bioisosteres further reveals the practical utility of this strategy.

Synthesis of Quinazolines from N,N′-Disubstituted Amidines via I2/KI-Mediated Oxidative C-C Bond Formation

An I2/KI-promoted oxidative C-C bond formation reaction from C(sp3)-H and C(sp2)-H bonds has been used to construct quinazoline skeletons from N,N′-disubstituted amidines. The required substrates are readily prepared from the corresponding acyl chlorides, anilines, and alkyl/benzylamines by sequential amidation, chlorination, and amination reactions. Under the optimal oxidative cyclization conditions, all these amidines were conveniently transformed into the expected products in moderate to good yields. This practical and environmentally benign approach works well with crude amidine intermediates and can also be carried out on a gram scale.

Transition Metal-Free Visible Light-Driven Photoredox Oxidative Annulation of Arylamidines

A fast catalytic synthesis of multisubstituted quinazolines from readily available amidines via visible light-mediated oxidative C(sp3)-C(sp2) bond formation has been established. This reaction is a metal-free oxidative coupling catalyzed by a photoredox organocatalyst. The protocol features low catalyst loading (1 mol %).

Solvent/oxidant-switchable synthesis of multisubstituted quinazolines and benzimidazoles via metal-free selective oxidative annulation of arylamidines

A fast and simple divergent synthesis of multisubstituted quinazolines and benzimidazoles was developed from readily available amidines, via iodine(III)-promoted oxidative C(sp3)-C(sp2) and C(sp 2)-N bond formation in nonpolar and polar solvents, respectively. Further selective synthesis of quinazolines in polar solvent was realized by TEMPO-catalyzed sp3C-H/sp2C-H direct coupling of the amidine with K2S2O8 as the oxidant. No metal, base, or other additives were needed.