32700-71-3

Upstream product

• 201230-82-2 carbon monoxide 
• 615-43-0 2-iodophenylamine 
• 6620-80-0 N-isopropylbenzimidoyl chloride 
• 118-48-9 isatoic anhydride 
• 100-52-7 benzaldehyde 
• 75-31-0 isopropylamine 
• 30391-89-0 2-amino-N-isopropylbenzamide 
• 611-73-4 Benzoylformic acid 
• 64141-92-0 N-isopropyl-2-iodobenzamide 
• 100-47-0 benzonitrile 
• 108-88-3 toluene 
• 591-50-4 iodobenzene 
• 3476-67-3 3-isopropyl-3,4-dihydroquinazoline-4-one 
• 118-92-3 anthranilic acid 

Relevant academic research and scientific papers

α-Keto Acids as Triggers and Partners for the Synthesis of Quinazolinones, Quinoxalinones, Benzooxazinones, and Benzothiazoles in Water

A general and efficient method for the synthesis of quinazolinones, quinoxalinones, benzooxazinones, and benzothiazoles from the reactions of α-keto acids with 2-aminobenzamides, benzene-1,2-diamines, 2-aminophenols, and 2-aminobenzenethiols, respectively, is described. The reactions were conducted under catalyst-free conditions, using water as the sole solvent with no additive required, and successfully applied to the synthesis of sildenafil. More importantly, these reactions can be conducted on a mass scale, and the products can be easily purified through filtration and washing with ethanol (or crystallized).

KOtBu-BF3.OEt2 mediated synthesis of quinazolin-4(3H)-ones from 2-substituted amides with nitriles and aldehydes

KOtBu-BF3.OEt2 mediated synthesis of quinazolin-4(3H)-ones from 2-substituted amides with nitriles and aldehydes have been developed. In this protocol, a variety of nitriles as well as aldehydes react with 2-substituted benzamides to corresponding quinazolin-4(3H)-ones products in good to moderate yields, via the cleavage of C-X and C-N bonds and the formation of double C-N bonds simultaneously, in presence of potassium tert-butoxide.

Synthesis of 2-aryl quinazolinones: Via iron-catalyzed cross-dehydrogenative coupling (CDC) between N-H and C-H bonds

Herein, we describe the direct synthesis of quinazolinones via cross-dehydrogenative coupling between methyl arenes and anthranilamides. The C-H functionalization of the benzylic sp3 carbon is achieved by di-t-butyl peroxide under air, and the subsequent amination-aerobic oxidation process completes the annulation process. Iron catalyzed the whole reaction process and various kinds of functional groups were tolerated under the reaction conditions, providing 31 examples of 2-aryl quinazolinones using methyl arene derivatives in yields of 57-95percent. The synthetic potential has been demonstrated by the additional synthesis of aryl-containing heterocycles. This journal is

Cu/Pd-catalyzed C-2-H arylation of quinazolin-4(3H)-ones with (hetero)aryl halides

The regiospecific C-2-H arylation of N-3-substituted quinazolin-4(3H)-ones with a wide range of aryl or (hetero)aryl halides under microwave irradiation was studied. A ligand-dependent palladium/copper bicatalytic system was developed and allowed direct c

Reversible P(III)/P(V) redox: Catalytic aza-Wittig reaction for the synthesis of 4(3H)-quinazolinones and the natural product vasicinone

The catalytic aza-Wittig reaction based on a phosphine/phosphine oxide catalytic cycle is reported. The by-product triphenylphosphine oxide (Ph 3PO) was reduced in situ to triphenylphosphine (Ph3P) with good chemselectivity so that the aza-Wittig reaction can be accomplished by using merely a catalytic amount of triphenylphosphine. The reaction has been demonstrated in an efficient synthesis of 4(3H)-quinazolinones and the natural product (S)-vasicinone in high yields, by using a catalytic amount of triphenylphosphine (5%) and the tetramethyldisiloxane/titanium tetraisopropoxide [TMDS/Ti(O-i-Pr)4] reductant system (81-95% yields and >99% ee).

A practical and versatile approach toward a one-pot synthesis of 2,3-disubstituted 4(3H)-quinazolinones

An effective one-pot three-component route to 4(3H)-quinazolinones from commercially available starting materials is reported. Thus, isatoic anhydride reacted with ammonium acetate or primary amines and aldehydes in the presence of iodine to produce the corresponding quinazolinone derivatives in moderate to good yields. Springer-Verlag 2010.

Palladium-catalyzed cyclocarbonylation of o-lodoanilines with Imidoyl Chlorides to produce quinazolin-4(3H)-ones

A wide variety of substituted quinazolin-4(3H)-ones were prepared in 63-91% yields by the palladium-catalyzed cyclocarbonylation of o-iodoanilines with imidoyl chlorides and carbon monoxide. The reaction is believed to proceed via in situ formation of an amidine, followed by oxidative addition, CO insertion, and intramolecular cyclization to give the substituted quinazolin-4(3H)-ones.

Parallel fluorous biphasic synthesis of 3H-quinazolin-4-ones by an Aza-Wittig reaction employing perfluoroalkyl-tagged triphenylphosphine

A perfluoroalkyl-tagged triphenylphosphine was applied in a fluorous biphasic system for the efficient parallel synthesis of 3H-quinazolin-4-ones via an Aza-Wittig reaction. The products were isolated by solid-phase extraction on fluorous reversed-phase silica gel. A new solid-phase bound phosphine derivative was used for comparison and yielded similar results.

4(3H)-Quinazolinones from the reaction of N-arylnitrilium salts with isocyanates

N-Arylnitrilium salts 1 react with isocyanates 2 to give salts 3 of 4(3H)-quinazolinones 4, from which compounds 4 can be obtained with base. A metathesis of an isocyanate with a nitrilium salt is reported.

Studies on 4(1H)-quinazolinones. 5. Synthesis and antiinflammatory activity of 4(1H)-quinazolinone derivatives

A number of new 4(1H)-quinazolinones were synthesized and evaluated in the carrageenin-induced paw edema test. Most of the compounds were obtained by the cyclization of the appropriately substituted anthranilamides with acid chlorides, followed by further chemical transformation. Structure-activity data suggest that 2-isopropyl-1-phenyl-, 2-cyclopropyl-1-phenyl-, and 1-isopropyl-2-phenyl-4(1H)-quinazolinones afford optimal potency and the presence of a halogen atom is preferred for activity. Adrenalectomy does not affect the antiinflammatory test results. The best result taking into account both efficacy and side effects was displayed by 1-isoproyl-(2-fluorophenyl)-4(1H)-quinazolinone.