20877-83-2

Upstream product

• 100-52-7 benzaldehyde 
• 28144-70-9 anthranilic acid amide 
• 612-24-8 o-nitrobenzonitrile 

Downstream Products

• 20877-82-1 2-(aminomethyl)-N-benzylaniline 
• 1022-45-3 2-phenyl-4(3H)-quinazolinone 
• 40288-70-8 2-phenyl-4-phenylaminoquinazoline 
• 121998-76-3 2-phenyl-2,3-dihydro-4(1H)-quinazolinone 

Relevant academic research and scientific papers

Glucose as an Eco-Friendly Reductant in a One-Pot Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones

Carbohydrates such as glucose are an abundant renewable resource that can be employed in synthetic processes as a source of carbon and/or hydrogen to yield products of high economical and biological impact. Herein, we report a versatile and environmentally friendly protocol for the one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones, a privileged scaffold in medicinal chemistry, based on the use of glucose as an eco-friendly reductant in alkaline aqueous medium. This method can be viewed as a blueprint for the development of further one-pot sequences involving glucose as a reductant.

Adamantyl-BINOL as platform for chiral porous polymer aromatic frameworks. Multiple applications as recyclable catalysts

Herein, we report the synthesis of adamantyl-BINOL-based chiral porous aromatic polymers (Ad-BINOL-PAFs) for heterogeneous catalysis. Ad-BINOL-OH-PAF (365 m2·g?1 SABET) was built through the covalent bonds among of 4,4′-dibromo-O-ethyl-protected adamantyl-BINOL with 1,3,5-Triphenylbenzene-4′,4″,4′″-triboronic acid and in the presence of [Ti(OiPr)4] results an effective recyclable catalyst in the asymmetric addition of diethylzinc to aromatic aldehydes (ee up to 88%). The corresponding heterogenized phosphoric acid (Ad-BINOL-PO2H-PAF) was applied as heterogeneous recyclable organocatalyst for the cascade condensation/amine addition of anthranilamide with aldehydes and transfer hydrogenation reactions obtaining high yields but low enantioselectivity. On the other hand, heterogeneous phosphoric acid (Ad-BINOLs-PO2H-PAF) was also used as effective phosphate ligands for synthesis of rhodium(II) complexes which were effective catalysts in cyclopropanation of styrene affording chiral cyclopropanes in good yield and high diastereoselectivity (>99%) and moderate enantioselectivity (ee 50%).

Synthesis of 2-(hetero)arylquinazolinones in aqueous media

Mechanochemical treatment of N-unsubstituted or N-methyl anthranilamide with benzaldehyde yielded their Schiff bases derivatives which could be easily cyclized to the corresponding 2-phenyl-2,3-dihydroquinazolinones via thermal rearrangement in water. On the basis of the above findings, an eco-friendly method was applied to prepare quinazolin-4(1H)-one derivatives from anthranilamides and a number of (hetero)aryl aldehydes. Heating the aqueous mixture of starting compounds to 90 °C resulted in the products in 81-94% yields. All products precipitated from the reaction mixture and were isolated by simply filtration. No further work-up or purification was necessary.

Development of a New Synthetic Method for Quinazolinones via Aerobic Oxidation in dimethylsulfoxide

The present invention relates to a method for preparing quinazoline derivatives by aerobic oxidation using oxygen as an oxidizing agent in dimethylsulfoxide (DMSO) solvent wherein metal and base are excluded. The method for preparing quinazoline derivatives according to the present invention does not require any metal catalyst such as palladium or iridium, and thus does not cause toxicity problem of residual metal; and does not require demanding processes such as strong acid, or base conditions, low temperature reactions, or reactions of anhydrous conditions and thus, it is possible to simply and economically prepare quinazoline derivatives by reacting anthranilamide derivatives and an aldehyde source.

Sulfate Radical Anion (SO4?-) Mediated C(sp3)-H Nitrogenation/Oxygenation in N-Aryl Benzylic Amines Expanded the Scope for the Synthesis of Benzamidine/Oxazine Heterocycles

A transition-metal-free, K2S2O8-mediated intramolecular oxidative nitrogenation/oxygenation of C(sp3)-H in N-aryl benzylic amines followed by oxidation at the benzylic center has been developed for the synthesis of benzamidine/benzoxazine heterocycles, providing an expedient access to quinazolin-4(3H)-ones, N-aryl-2-arylbenzimidazoles, and 4H-3,1-benzoxazin-4-ones. A considerable amount of work dealing with the mechanistic study to understand the crucial intramolecular cyclization step largely favors an iminium ion as the key intermediate.

Synthesis of quinazolinones from anthranilamides and aldehydes via metal-free aerobic oxidation in DMSO

A highly environmentally benign protocol for the synthesis of quinazolinones from anthranilamides and aldehydes via aerobic oxidation was developed in wet DMSO. This protocol is operationally simple, exhibits broad substrate scope, and does not need toxic metal catalysts and bases. In addition, the utility of this transformation was further demonstrated by converting the resulting quinazolinones into other useful products in the same-pot without their isolation.

Investigation of the enantioselective synthesis of 2,3- Dihydroquinazolinones Using Sc(III)- Inda -pybox

Derivatives of 2,3-dihydroquinazolinones (2,3-DHQZs) are prized for their prevalent pharmaceutical applications. Although there are potential applications, methods available for the enantioselective synthesis of these valuable compounds are scarce, since the chiral aminal center is prone to racemization. We have overcome the difficulties in the catalytic enantioselective synthesis of 2,3-DHQZs using Sc(III)-inda-pybox as a catalyst, in a process with a broad substrate scope. Georg Thieme Verlag Stuttgart. New York.