506418-75-3

Usage

Synthesis Reference(s)

Synthesis, p. 2292, 2003 DOI: 10.1055/s-2003-42409

Upstream product

• 4919-43-1 1-amino-2-naphthoic acid 
• 77287-34-4 formamide 
• 230-28-4 benzo[h]quinazoline 
• 76056-13-8 2,2-dimethyl-N-(naphthalen-1-yl)propanamide 
• 1619257-81-6 ethyl 1-[(tert-butoxycarbonyl)amino]naphthalene-2-carboxylate 
• 1619257-83-8 ethyl 1-[(2,2-dimethylpropanoyl)amino]naphthalene-2-carboxylate 
• 1184003-27-7 1-aminonaphthalene-2-carboxylic acid ethyl ester 
• 72594-62-8 naphthalen-1-yl-carbamic acid tert-butyl ester 
• 34773-06-3 5,6-dihydrobenzo[h]quinazoline 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 3100-67-2 1-amino-2-naphthalenecarbonitrile 
• 86-57-7 1-Nitronaphthalene 
• 236093-41-7 1,2,5,6-tetrahydro-2-thioxobenzo[h]quinazolin-4(3H)-one 
• 7442-52-6 methyl 1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate 

Downstream Products

• 1456819-70-7 (benzo[h]quinazolin-4-yl)-(3-trifluoromethylphenyl)amine hydrochloride 
• 1456819-69-4 (benzo[h]quinazolin-4-yl)-(3-methylphenyl)amine hydrochloride 
• 1456819-68-3 (benzo[h]quinazolin-4-yl)-(3-bromophenyl)amine hydrochloride 

Relevant academic research and scientific papers

Organometallic complex, light-emitting element, light-emitting device, electronic device, and lighting device

A novel substance capable of emitting phosphorescence is provided. An organometallic complex represented by General Fomulae (G3) or (G5). In the formulae, M represents iridium, platinum, palladium, or rhodium, R1 represents a substituted or uns

Substituted benzoquinazolinones. Part 1: Synthesis of 6-aminobenzo[h] quinazolinones via Buchwald-Hartwig amination from 6-bromobenzo[h]quinazolinones

6-(Morpholin-4-yl)benzo[h]quinazolin-4(3H)-one derivatives 18a,b were prepared under Buchwald-Hartwig conditions by reacting 6-bromobenzo[h] quinazolin-4(3H)-ones 13a,b with morpholine in the presence of a Pd(OAc) 2/XantPhos system in 1,4-dioxane as solvent. The starting 6-bromobenzo[h]quinazolin-4(3H)-ones 13 were synthesized via condensation of the ethyl 1-amino-4-bromonaphthalene-2-carboxylate (11) with formamide (Niementowski reaction), and then reaction of the obtained benzoquinazolinone 9 with appropriates benzyl bromides. Compound 11 was prepared using a three-step procedure involving (a) metalation of the N-Boc- or N-Piv-protected 1-aminonaphthalenes with t-BuLi, followed by reaction with ethyl chloroformate, (b) bromination of the naphthalene ring of ester 3 using NBS, and next (c) deprotecion of the amine group with TFA or HCl. Biological screening of the potential cytotoxicity of compounds 8, 9, 18b on A549 and HT29 cell lines, as well as on the lymphocytes showed that compound 18b has interesting anticancer activities. The detailed synthesis, spectroscopic data, and biological assays were reported.

Substituted benzoquinazolinones. Part 1: Synthesis of 6-aminobenzo[h]quinazolinones via Buchwald-Hartwig amination from 6-bromobenzo[h]quinazolinones

6-(Morpholin-4-yl)benzo[h]quinazolin-4(3H)-one derivatives 18a,b were prepared under Buchwald-Hartwig conditions by reacting 6-bromobenzo[h]quinazolin-4(3H)-ones 13a,b with morpholine in the presence of a Pd(OAc)2/XantPhos system in 1,4-dioxane as solvent. The starting 6-bromobenzo[h]quinazolin-4(3H)-ones 13 were synthesized via condensation of the ethyl 1-amino-4-bromonaphthalene-2-carboxylate (11) with formamide (Niementowski reaction), and then reaction of the obtained benzoquinazolinone 9 with appropriates benzyl bromides. Compound 11 was prepared using a three-step procedure involving (a) metalation of the N-Boc- or N-Piv-protected 1-aminonaphthalenes with t-BuLi, followed by reaction with ethyl chloroformate, (b) bromination of the naphthalene ring of ester 3 using NBS, and next (c) deprotecion of the amine group with TFA or HCl. Biological screening of the potential cytotoxicity of compounds 8, 9, 18b on A549 and HT29 cell lines, as well as on the lymphocytes showed that compound 18b has interesting anticancer activities. The detailed synthesis, spectroscopic data, and biological assays were reported.

Quinazoline-based multi-tyrosine kinase inhibitors: Synthesis, modeling, antitumor and antiangiogenic properties

In this work the synthesis and the biological evaluation of some novel anilinoquinazoline derivatives carrying modifications in the quinazoline scaffold and in the aniline moiety were reported. Preliminary cytotoxicity studies identified three derivatives

Benzoquinazoline derivatives as new agents affecting DNA processing

A new series of benzo[h]quinazoline and benzo[f]quinazoline derivatives was prepared and studied for the biological activity. The compounds carrying a dimethylaminoethyl side chain (6c, 8c and 12) inhibit cell growth. The ability to form a molecular compl

An Expedient Synthesis of Benzo[h]quinazolin-4(3H)-one: Structure of Samoquasine A Revisited

An expedient four-step synthesis of benzo[h]quinazolin-4(3H)-one (1) starting from 1-tetralone is reported. The claimed identity of samoquasine A with perlolidine (4) has been discussed in the light of the present synthesis.

Total synthesis of 3,4-dihydrobenzo[h]quinazolin-4-one and structure elucidation of perlolidine and samoquasine A

The total synthesis of 3,4-dihydrobenzo[h]quinazolin-4-one is described. Based on the spectral data and chemical evidence, the structures of 3,4-dihydrobenzo[h]quinazolin-4-one, perlolidine, and samoquasine A are not the same. A structure for samoquasine A is suggested.