134408-32-5

Basic information

• Product Name: 4-(4-methoxyphenyl)-3,4,5,6-tetrahydrobenzo[h]quinazoline-2(1H)-thione
• Synonyms: 4-(4-methoxyphenyl)-3,4,5,6-tetrahydrobenzo[h]quinazoline-2(1H)-thione
• CAS NO: 134408-32-5
• Molecular Formula: C₁₉H₁₈N₂OS
• Molecular Weight: 322.42402
• Mol File: 134408-32-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-(4-methoxyphenyl)-3,4,5,6-tetrahydrobenzo[h]quinazoline-2(1H)-thione(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-methoxyphenyl)-3,4,5,6-tetrahydrobenzo[h]quinazoline-2(1H)-thione(134408-32-5)
• EPA Substance Registry System: 4-(4-methoxyphenyl)-3,4,5,6-tetrahydrobenzo[h]quinazoline-2(1H)-thione(134408-32-5)

Safety Data

• Hazardous Substances Data: 134408-32-5(Hazardous Substances Data)

Upstream product

• 49629-37-0 (E)-2-(4-methoxybenzylidene)-3,4-dihydro-2H-naphthalen-1-one 
• 17356-08-0 thiourea 
• 123-11-5 4-methoxy-benzaldehyde 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 49629-37-0 2-(4-methoxybenzylidene)-1-tetralone 

Downstream Products

• 1628798-79-7 3-(7-(4-methoxyphenyl)-6,7-dihydro-5H-benzo[h]thiazolo[2,3-b]-quinazolin-9-yl)-2H-chromen-2-one 
• 488087-52-1 9-(4-bromophenyl)-7-(4-methoxyphenyl)-6,7-dihydro-5H-benzo[h]thiazolo[2,3-b]quinazoline 
• 797764-46-6 9-(4-chlorophenyl)-7-(4-methoxyphenyl)-6,7-dihydro-5H-benzo[h]thiazolo[2,3-b]quinazoline 
• 157282-77-4 7-(4-methoxyphenyl)-5,7-dihydro-6H-10-thia-7a,11-diaza-cyclopenta[b]phenanthren-8-one 
• 134408-35-8 3-methyl-2-methylmercapto-4-phenyl-3,4,5,6-tetrahydrobenzoquinazoline 

Relevant articles and documents

Green chemistry preparation of thiochromeno[4,3-b]pyran and benzo[h]thiazolo[2,3-b]quinazoline derivatives using HSBM technique over ZnAl2o4 nano-powders

Aim and Objective: The aim of this paper is to introduce HSBM as a green and environmentally friendly technique for the synthesis of thiochromeno[4,3-b]pyran and benzo[h]thiazolo[2,3-b]quinazoline derivatives over ZnAl2O4 nanopowders

Base-mediated one-pot synthesis of 3,4,5,6-tetrahydro-4-substituted benzo[h]quinazoline-2(1H)-thione derivatives and evaluation of their antioxidant activity

One-pot three-component Beginelli-like reactions of a ketone 1, an aryl aldehyde 2, and thiourea 3 in the presence of sodium hydroxide are described. In this reaction, 3,4,5,6-tertrahydro-4-substituted quinazoline-2(1H)-thione derivatives 4a–h were obtain

Benzo[h]thiazolo[2,3-b]quinazolines by an efficient p-toluenesulfonic acid-catalyzed one-pot two-step tandem reaction

A highly efficient method has been developed for synthesis of 7,9-disubstituted-6,7-dihydro-5H-benzo[h]thiazolo[2,3-b]quinazolines via multicomponent one-pot two-step tandem reaction involving 1-tetralone, arylaldehydes, thiourea, and 4-chlorophenacyl bromide/(3-bromoacetyl)coumarin utilizing p-toluenesulfonic acid as catalyst in glacial acetic acid under reflux conditions. Analytically pure products are formed with excellent yield and short reaction time. All the synthesized compounds were confirmed by their spectral and elemental analyses. Graphical abstract: [Figure not available: see fulltext.]

Synthesis, characterization and biological evaluation of fused thiazolo[3,2-a]pyrimidine derivatives

A series of fused thiazolo[3,2-a]pyrimidines (7a-g, 8a-f, 11a-g and 12a,b) have been synthesized in good yields by reaction of fused 3,4-dihydropyrimidin- 2(1H)-thiones (4a-g) with phenacyl bromides (5,6)/3-(2-bromoacetyl)coumarins (9,10) under conventional heating in acetic acid. Analytical and spectral studies as well as single crystal X-ray diffraction data on the representative compound 8e confirmed the structure of all the reaction products. All the synthesized compounds were screened for their antibacterial, antioxidant and DNA cleavage activities. The compound 7e against Escherichia coli, 8a and 8c-e against Pseudomonas aeruginosa have shown prominent antibacterial activity compared to the standard drug Penicillin with MIC 9.375 μg mL-1, whereas the compounds 11c, 12a and 12b have shown very good antioxidant activity compared to the standard drug Trolox with IC50 values 12.36, 11.12 and 13.88 μM respectively. Compounds 11f and 12b have completely cleaved the DNA even at 50 μg mL-1 concentration and the remaining compounds have partially cleaved the DNA.

Synthesis of fused thiazolo[3,2-a]pyrimidinones: N-aryl-2-chloroacetamides as doubly electrophilic building blocks

2-Chloro-N-phenylacetamide and N-(benzo[d]thiazol-2-yl)-2-chloroacetamide are doubly electrophilic building blocks for the formation of ring annulated thiazolo[3,2-a]pyrimidinone products. This synthetic route involves formation of the title compound in acceptable product yields by the elimination of the by-product, aniline/2-aminobenzothiazole. Analytical and spectral studies, as well as single crystal X-ray data on the representative compound 6c confirmed the structure of all the reaction products.

Efficient ionic liquid-catalysed synthesis and antimicrobial studies of 4,6-diaryl- and 4,5-fused pyrimidine-2-thiones

One-pot three-component condensation of aromatic ketones (1-tetralones, acetophenones, indane-1,3-dione), substituted aromatic aldehydes and thiourea in the presence of N-methylpyridinium tosylate under solvent free conditions at 100-110 °C for 2-4 h afforded tetrahydrobenzo[h]quinazoline-2-thiones, pyridimidine-2-thiones and indeno-pyrimidine-2-thiones in excellent yields. All synthesised thiones were screened for their antimicrobial activities.

Heterocyclic systems containing bridgehead nitrogen atom: Part LXXV - Syntheses of thiazolobenzoquinazolines and thiazinobenzoquinazolines

2-Arylidenetetralin-1-ones (1a-c) on condensation with thiourea give 4-aryl-3,4,5,6-tetrahydrobenzoquinazoline-2(1H)-thiones (2a-c) which on reaction with chloroacetic acids, α- and β-halopropionic acids afford 5-aryl-2,3,6,7-tetrahydro-3-oxo-5H-thiazo

On the Tautomerism of 2,4-Disubstituted 3,4,5,6-Tetrahydrobenzoquinazolines

The tautomerism of the title compounds was investigated by 1H-, 13C-NMR and UV spectroscopy.Compound 5 was compared with respect to its spectra with those of appropriate model compounds 1,3,4, and 6.This gave evidence that 5 predominates in the tautomeric