1208259-10-2

Upstream product

• 26260-02-6 2-iodobenzaldehyde 
• 38980-96-0 4-(trifluoromethyl)benzimidamide hydrochloride 
• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 4403-69-4 2-amino-1-benzylamine 
• 5344-90-1 2-Aminobenzyl alcohol 
• 3300-51-4 p-Trifluoromethylbenzylamine 
• 455-18-5 4-CF₃C₆H₄CN 
• 157869-15-3 2-((4-methoxyphenyl)ethynyl)aniline 
• 13939-06-5 molybdenum hexacarbonyl 
• 100-46-9 benzylamine 
• 1891-90-3 p-trifluoromethylbenzamide 
• 50-00-0 formaldehyd 
• 201230-82-2 carbon monoxide 
• 402-43-7 p-trifluoromethylphenyl bromide 

Downstream Products

• 1451359-94-6 (E)-4-styryl-2-(4-(trifluoromethyl)phenyl)quinazoline 

Relevant academic research and scientific papers

Synthesis of quinazolines from (2-aminoaryl)methanols and arylmethanamines catalyzed by rhodium complex

Efficient synthesis of quinazoline derivatives via rhodium-catalyzed dehydrogenation and ring-closing method was developed with moderate to high yields.

A convenient palladium-catalyzed carbonylative synthesis of quinazolines from 2-aminobenzylamine and aryl bromides

A novel and practical strategy towards quinazoline scaffolds synthesis has been achieved. Through palladium-catalyzed carbonylative coupling of 2-aminobenzylamine with aryl bromides, the desired quinazolines were produced in moderate to good yields for the first time. The reactions followed an aminocarbonylation-condensation-oxidation sequence in a one-pot one-step manner. Preliminary investigation showed DMSO serves both as solvent and oxidant in this procedure.

BTP-Rh@g-C3N4 as an efficient recyclable catalyst for dehydrogenation and borrowing hydrogen reactions

Highly active catalysts play an important role in modern catalysis. A novel and efficient ligand benzotriazole-pyrimidine (BTP) and the corresponding rhodium composite on C3N4 were successfully synthesized. The resulting rhodium composite was fully characterized by scanning electron microscopy (SEM), transmission electron microscopy (TEM), x-ray diffraction (XRD), thermogravimetric analysis (TGA), and x-ray photoelectron spectroscopy (XPS). The obtained composite exhibited good catalytic activity and good recovery performance in the synthesis of quinoxaline from 2-aminobenzyl alcohol and benzonitrile, and more than 20 quinoxalines were obtained in good yields. Additionally, it also showed that rhodium composite could achieved good catalytic performance in the synthesis of functionalized ketone through borrowing hydrogen strategy.

Palladium-catalyzed carbonylative synthesis of quinazolines: Silane act as better nucleophile than amidine

A palladium-catalyzed reductive carbonylation reaction has been developed for the synthesis of quinazolines. With N-(2-iodophenyl)benzimidamide as starting materials, a series of quinazolines were obtained through the aromatic aldehyde intermediates in moderate to good yields with good functional group compatibilities. In this system, silane act as better nucleophile than amidine.

Nickel-Catalyzed [4 + 2] Annulation of Nitriles and Benzylamines by C-H/N-H Activation

Nickel-catalyzed [4 + 2] annulation of benzylamines and nitriles via C-H/N-H bond activation, providing straightforward atom-economic access to a wide variety of multisubstituted quinazolines, is reported. Mechanistic investigation revealed that the in situ formed amidines from the coupling of benzylamines and nitriles direct the nickel catalyst to activate the ortho-C-H bond of the phenyl ring of the benzylamine.

Efficient synthesis of quinazolines by the iron-catalyzed acceptorless dehydrogenative coupling of (2-aminophenyl)methanols and benzamides

The acceptorless dehydrogenation coupling (ADC) of (2-aminophenyl)methanols with benzamides was achieved with catalytic FeCl2·4H2O in an efficient synthesis of quinazolines. This simple catalytic system is atom-economical, environmentally benign and suited to a variety of substrates.

Highly Ordered Mesoporous Cobalt Oxide as Heterogeneous Catalyst for Aerobic Oxidative Aromatization of N-Heterocycles

N-heterocycles are key structures for many pharmaceutical intermediates. The synthesis of such units normally is conducted under homogeneous catalytic conditions. Among all methods, aerobic oxidative aromatization is one of the most effective. However, in homogeneous conditions, catalysts are difficult to be recycled. Herein, we report a heterogeneous catalytic strategy with a mesoporous cobalt oxide as catalyst. The developed protocol shows a broad applicability for the synthesis of N-heterocycles (32 examples, up to 99 % yield), and the catalyst presents high turnover numbers (7.41) in the absence of any additives. Such a heterogenous approach can be easily scaled up. Furthermore, the catalyst can be recycled by simply filtration and be reused for at least six times without obvious deactivation. Comparative studies reveal that the high surface area of mesoporous cobalt oxide plays an important role on the catalytic reactivity. The outstanding recycling capacity makes the catalyst industrially practical and sustainable for the synthesis of diverse N-heterocycles.

Dehydrogenative Synthesis of Quinolines, 2-Aminoquinolines, and Quinazolines Using Singlet Diradical Ni(II)-Catalysts

Simple, straightforward, and atom economic methods for the synthesis of quinolines, 2-aminoquinolines, and quinazolines via biomimetic dehydrogenative condensation/coupling reactions, catalyzed by well-defined inexpensive and easy to prepare singlet diradical Ni(II)-catalysts featuring two antiferromagnetically coupled singlet diradical diamine type ligands are described. Various polysubstituted quinolines, 2-aminoquinolines, and quinazolines were synthesized in moderate to good yields from different low-cost and readily accessible starting materials. Several control experiments were carried out to get insight into the reaction mechanism which shows that the nickel and the coordinated diamine ligands participate in a synergistic way during the dehydrogenation of alcohols.

NNN pincer Ru(II)-catalyzed dehydrogenative coupling of 2-aminoarylmethanols with nitriles for the construction of quinazolines

An efficient NNN pincer Ru(II)-catalyzed preparation of quinazolines via acceptorless dehydrogenative strategy has been developed. Under the optimized conditions, a broad range of substituted o-aminobenzyl alcohols and (hetero)aryl or alkyl nitriles were well tolerated to afford various 2-substituted quinazolines in high yields. Subsequently, a set of control experiments have been performed to elucidate the reaction mechanism, which underwent alcohol oxidation, nitrile hydration, and cyclocondensation steps. The current protocol is featured with several advantages, such as environmental benignity, operational simplicity, broad substrate scope (compatible with aliphatic nitriles, up to 87% yield), and short reaction time (mostly in 2 h).

Synergistic catalysis on Fe-N: X sites and Fe nanoparticles for efficient synthesis of quinolines and quinazolinones via oxidative coupling of amines and aldehydes

In this paper, we developed a reusable heterogeneous non-precious iron nanocomposite comprising metallic Fe-Fe3C nanoparticles and Fe-Nx sites on N-doped porous carbon, which allows for highly efficient synthesis of quinolines and quinazolinones via oxidative coupling of amines and aldehydes using H2O2 as the oxidant in aqueous solution under mild conditions. A set of quinazolines and quinazolinones were synthesized in high yields with a broad substrate scope and good tolerance of functional groups. Characterization and control experiments disclose that a synergistic effect between the metallic Fe nanoparticles and built-in Fe-Nx sites is primarily responsible for the outstanding catalytic performance. Furthermore, the iron nanocomposite could be readily recovered for successive use without appreciable loss in catalytic activity and selectivity. This work provides an expedient and sustainable method to access pharmaceutically relevant N-heterocycles.