1022-44-2

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 36, p. 1463, 1971 DOI: 10.1021/jo00810a004

Upstream product

• 59456-01-8 4-bromo-2-phenylquinazoline 
• 6499-41-8 5-phenyltetrazolo<1,5-c>quinazoline 
• 100-47-0 benzonitrile 
• 1885-29-6 anthranilic acid nitrile 
• 420-04-2 CYANAMID 
• 4903-36-0 N-phenyl-benzimidoyl chloride 
• 94079-21-7 2-Amino-N-benzoylbenzamidin 
• 82216-65-7 3-(2-benzylaminophenyl)-5-phenyl-1,2,4-oxadiazole 
• 7510-49-8 methyl 2-(benzamido)benzoate 
• 117998-85-3 2-phenyl-4(1H)-quinazolone-oxime 
• 158832-74-7 1-amino-1-chloro-3,5-diphenyl-2,4-diaza-1,3-butadiene 
• 104-94-9 4-methoxy-aniline 
• 400053-10-3 1-(4-methoxyphenyl)-3-(2-phenylquinazolin-4-yl) thiourea 
• 400604-97-9 N³,N³-(3-oxapentan-1,5-diyl)-N¹-(2-phenyl-3,4-dihydroquinazolin-4-yliden)thiourea 

Downstream Products

• 1022-45-3 2-phenyl-4(3H)-quinazolinone 
• 117998-85-3 2-phenyl-4(1H)-quinazolone-oxime 
• 94078-82-7 N-(2-phenylquinazolin-4-yl)benzamide 
• 1290545-20-8 1-(4-(N,N-bis(2-chloroethyl)amino)phenyl)-3-(2-phenylquinazolin-4-yl)urea 

Relevant academic research and scientific papers

Isoquinoline and quinazoline urea analogues as antagonists for the human-adenosine A3 receptor

Isoquinoline and quinazoline urea derivatives were found to bind to human adenosine AS receptors. Series of N-phenyl-N'-quinazolin-4-ylurea derivatives and N-phenyl-N'-isoquinolin-1-ylurea derivatives were synthesized and tested in radioligand binding ass

Reactivity study on morpholine-1-carbothioic acid (2-phenyl-3H-quinazolin-4-ylidene) amide

Regioselective reactions of morpholine-1-carbothioic acid (2-phenyl-3H-quinazolin-4-ylidene) amide (1) with electrophiles and nucleophiles were studied. The compound (1) reacts with alkyl halides in basic medium to afford S-substituted isothiourea derivat

Efficient three-component synthesis of 4-aminoquinazolines

4-Aminoquinazolines were synthesized in good yields via a one-pot, three-component reaction of anthranilonitrile, acylchlorides, and ammonium acetate in the presence of catalytic amounts silica-supported Preyssler nanoparticles under refluxing conditions.

Synthesis of novel 5-phenylimidazo[1,2-c]quinazolin-3-amine derivatives via Groebke-Blackburn-Bienayme multicomponent reaction

We have developed an efficient and environmentally benign one-pot procedure for synthesis of novel N-alkyl-2-aryl-5-phenylimidazo[1,2-c]quinazolin-3-amine derivatives by use of the Groebke-Blackburn-Bienayme multicomponent reaction. The title compounds we

Synthesis and biological evaluation of quinazoline derivatives – A SAR study of novel inhibitors of ABCG2

Multidrug resistance (MDR) is a major obstacle for effective chemotherapeutic treatment of cancer frequently leading to failure of the therapy. MDR is often associated with the overexpression of ABC transport proteins like ABCB1 or ABCG2 which efflux harmful substances out of cells at the cost of ATP hydrolysis. One way to overcome MDR is to apply potent inhibitors of ABC transporters to restore the sensitivity of the cells toward cytostatic agents. This study focusses on the synthesis and evaluation of novel 2,4-disubstituted quinazoline derivatives regarding the structure-activity-relationship (SAR), their ability to reverse MDR and their mode of interaction with ABCG2. Hence, the inhibitory potency and selectivity toward ABCG2 was determined. Moreover, the intrinsic cytotoxicity and the reversal of MDR were investigated. Interaction type studies with the substrate Hoechst 33342 and conformational analyses of ABCG2 with 5D3 monoclonal antibody were performed for a better understanding of the underlying mechanisms. In our study we could further enhance the inhibitory effect against ABCG2 (compound 31, IC50: 55 nM) and identify the structural features that are crucial for inhibitory potency, the impact on transport activity and binding to the protein.

Palladium-Catalyzed Synthesis of 4-Aminoquinazolines from Amide Oxime Ethers and 2-Iodobenzonitrile

4-Substituted O-benzyl benzamide oximes reacted with 2-iodobenzonitrile in the presence of 0.1 mol % of [Pd2(dba)3], 0.2 mol % of XantPhos, and 1.5 equiv of Cs2CO3 in dioxane under argon to give 2-arylquinazolin

Efficient synthesis of 2-arylquinazolin-4-amines via a copper-catalyzed diazidation and ring expansion cascade of 2-arylindoles

Copper-catalyzed synthesis of 2-arylquinazolin-4-amines from readily available 2-arylindoles and TMSN3 has been developed. The mechanism study shows that the domino reaction may involve a free radical diazidation, denitrogenation, intramolecular cyclization and ring expansion sequence.

A Highly Efficient Copper-Catalyzed Three-Component Synthesis of 4-Aminoquinazolines

A highly efficient copper-catalyzed one-pot protocol is developed for the synthesis of 4-aminoquinazolines from easily available 2-iodo- or 2-bromobenzimidamides, aldehydes, and sodium azide. This one-pot approach proceeds via consecutive copper-catalyzed SNAr substitution, reduction, cyclization, oxidation and tautomerization. The corresponding target products (26 examples) are obtained in 50-90% yield.

Suzuki–Miyaura coupling of quinazolines containing an unprotected NH2 group: Synthesis and biological testing of quinazoline derivatives

A robust approach to 4-amino quinazoline bi-aryl compounds was developed through Suzuki–Miyaura coupling reaction of quinazoline containing an unprotected NH2 group and arylboronic acids. Pd(dcpf)Cl2 was found to be an efficient catalyst for the reaction. All the compounds were evaluated for antimicrobial activity against gram-positive and gram-negative bacteria and fungi. One of the compounds, 3l, found to be more active against Candida albicans than the standard Miconazole.

Quinazoline synthesis via Rh(III)-catalyzed intermolecular C-H functionalization of benzimidates with dioxazolones

An efficient double C-N bond formation sequence to prepare highly substituted quinazolines utilizing benzimidates and dioxazolones under the catalytic redox-neutral [Cp?RhCl2]2/AgBF4 system, where dioxazolones could work as an intern