59870-45-0

Upstream product

• 110-89-4 piperidine 
• 607-68-1 2,4-dichloroquinazoline 
• 858235-57-1 2-chloro-4-[(4-chlorophenyl)thio]quinazoline 

Downstream Products

• 1095659-04-3 4-(Piperidin-1-yl)-N-(4-(trifluoromethyl)benzyl)quinazolin-2-amine hydrochloride 

Relevant academic research and scientific papers

Nucleophile-nucleofuge duality of azide and arylthiolate groups in the synthesis of quinazoline and tetrazoloquinazoline derivatives

5-Arylthio-tetrazolo[1,5-c]quinazolines (tautomers of 2-arylthio-4-azido-quinazolines) undergo facile nucleophilic aromatic substitution reactions with amines, alcohols and alkylthiols. This, combined with the recently reported arylsulfanyl group dance, provides straightforward access to 4-azido-2-N-,O-,S-substituted quinazolines and/or their tetrazolo tautomers from commercially available 2,4-dichloroquinazoline. The azidoazomethine-tetrazole tautomeric equilibrium and the electron-withdrawing character of the fused tetrazolo system plays a central role in the developed transformations. 5-Amino-substituted tetrazolo[1,5-c]quinazolines undergo media-controlled tautomeric equilibrium, which permits them to demonstrate the reactivity traditionally associated with the azido substituent. Furthermore, a method for 5-O-substitited tetrazolo[1,5-a]quinazolines from 2,4-diazidoquinazoline was developed during the structural elucidation of the substitution products. The developed methodology will facilitate medicinal chemistry investigations into quinazoline derivatives and the discovered fluorescent properties of some of the products (e.g., 4-(4-phenyl-1H-1,2,3-triazol-1-yl)-2-(4-methylpiperazin-1-yl)quinazoline:λem.= 461 nm,ΦDCM= 0.89) could serve as a starting point for their further applications in analytical and materials science.

Synthesis of novel 1,5-disubstituted pyrrolo[1,2-: A] quinazolines and their evaluation for anti-bacterial and anti-oxidant activities

A new series of 1,5-disubstituted pyrrolo[1,2-a]quinazoline derivatives were prepared from 2-chloro-4-substituted quinazolines, propargyl alcohol, and secondary amines through novel multi-component reactions. These one-pot reactions, carried out in the presence of a palladium-copper catalyst, provide an efficient method for the synthesis of functionalized pyrrolo[1,2-a]quinazolines in good-to-high yields. A number of synthesized compounds were screened for their in vitro anti-bacterial activity against Gram-positive and Gram-negative bacteria using a well-diffusion method. Also the anti-oxidant activity of the products was evaluated using the DPPH (2,2-diphenyl-2-picrylhydrazyl) assays.

USE OF COMPOUNDS FOR PREPARING ANTI-TUBERCULOSIS AGENTS

Compounds of a compound of compound of general formula (I) wherein X1, X2, A, R1R2, R3 and R4 are as defined herein; are useful as anti-mycobacterial agents, especially agents for the treatment of tuberculosis.

Synthesis and bioactivities of novel piperidylpyrimidine derivatives: Inhibitors of tumor necrosis factor-alpha production

New piperidylpyrimidine derivatives, including quinazolines, were prepared, and their abilities to inhibit TNF-α production evaluated. Some compounds showed potent inhibitory activity in mouse macrophages stimulated with LPS. The synthesis and structure-activity relationships of these compounds are described. (C) 2000 Elsevier Science Ltd. All rights reserved.

2-4-DIAMINOQUINAZOLINES AS ANTITHROMBOTIC AGENTS

2,4-diaminoquinazolines are employed as antithrombotic agents and have the following general formula: SPC1Wherein R 1 and R 2 are monovalent groups independently selected from the group consisting of EQU1 wherein R 4 and R 5 independently are selected from the group consisting of hydrogen, alkyl, and cycloalkyl, with the proviso that both R 4 and R 5 cannot be cycloalkyl, EQU2 wherein R 6, R 7, and R 8 independently are selected from the group consisting of hydrogen and alkyl, and A is a divalent organic group having from two to about six carbon atoms such that the two nitrogen atoms are separated by at least two carbon atoms, and C. heterocyclic-amino, andR 3 is a monovalent group selected from the group consisting of hydrogen, halogen, and alkyl.