530-53-0

Basic information

• Product Name: 2,3-trimethylene-4-quinazolone
• Synonyms: 2,3-trimethylene-4-quinazolone;Pyrrolo[2,1-b]quinazolin-9(1H)-one,2,3-dihydro-
• CAS NO: 530-53-0
• Molecular Formula: C₁₁H₁₀N₂O
• Molecular Weight: 186.21
• Mol File: 530-53-0.mol
• Article Data: 73

Chemical Properties

• Boiling Point: 345.3°Cat760mmHg
• Flash Point: 162.6°C
• Appearance: /
• Density: 1.36g/cm³
• Vapor Pressure: 6.2E-05mmHg at 25°C
• Refractive Index: 1.709
• CAS DataBase Reference: 2,3-trimethylene-4-quinazolone(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-trimethylene-4-quinazolone(530-53-0)
• EPA Substance Registry System: 2,3-trimethylene-4-quinazolone(530-53-0)

Safety Data

• Hazardous Substances Data: 530-53-0(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 58, p. 310, 1993 DOI: 10.1021/jo00054a008

InChI:InChI=1/C11H10N2O/c14-11-8-4-1-2-5-9(8)12-10-6-3-7-13(10)11/h1-2,4-5H,3,6-7H2

Upstream product

• 616-45-5 2-pyrrolidinon 
• 5651-41-2 N-hydroxymethyl-anthranilic acid-lactone 
• 5264-35-7 2-methoxy-1-pyrroline 
• 118-92-3 anthranilic acid 
• 495-59-0 deoxypeganine 
• 500730-56-3 2-(3-phenoxy-propyl)-3H-quinazolin-4-one 
• 89140-13-6 2,3-trimethylene-1,2-dihydroquinazolinium picrate 
• 6346-09-4 4-aminobutyrylaldehyde diethylacetal 
• 529-23-7 o-aminobenzaldehyde 
• 201230-82-2 carbon monoxide 
• 615-43-0 2-iodophenylamine 
• 35387-16-7 (+/-)-vasicinone 
• 65636-69-3 9-chlorodeoxyvasicinone 
• 108-95-2 phenol 

Downstream Products

• 55727-59-8 2-(pyrrolidin-1-ylmethyl)benzenamine 
• 486-64-6 (S)-3-hydroxy-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one 
• 119364-42-0 (R)-3-hydroxy-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one 
• 95235-23-7 3-[1-Hydroxy-1-phenyl-meth-(Z)-ylidene]-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one 
• 98262-87-4 Benzoic acid [9-oxo-1,2-dihydro-9H-pyrrolo[2,1-b]quinazolin-(3Z)-ylidene]-phenyl-methyl ester 
• 133566-53-7 1-benzoyl-1,2-dihydrodeoxyvasicinone 
• 18549-16-1 C₁₈H₁₄N₂O 
• 1447710-22-6 (3E)-(3,4,5-trimethoxybenzylidene)-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one 
• 1447710-24-8 (3E)-3-(3,4-dimethoxybenzylidene)-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one 
• 1447710-26-0 (3E)-3-(2,5-dimethoxybenzylidene)-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one 
• 1164557-86-1 (3E)-3-(2-nitrobenzylidene)-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one 
• 1447710-30-6 (3E)-3-(2,3-dimethoxybenzylidene)-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one 

Relevant articles and documents

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Insight into the chemical bonding and electrostatic potential: A charge density study on a quinazoline derivative

2,3-Trimethylene-3,4-dihydroquinazoline shares the heterocyclic core with natural compounds and synthetic drugs. The hydrochloride of the compound forms excellent dihydrate crystals which have allowed us to collect high-resolution X-ray diffraction data and obtain the experimental charge density. The solid may be understood as built up from pairs of heterocyclic cations and chloride anions; a direct hydrogen bond links the halide to the formally cationic pyrimidine NH group. The hydrate water molecules interact with the anions, forming an infinite chain along the crystallographic a axis between the stacks of the heterocyclic cations. Based on the experimental charge density, a dipole moment of 16.1 Debye is calculated for a pair of the hydrogen-bonded quinazolinium cation and the chloride anion in the extended crystal structure.

Synthesis, characterization, and antimicrobial activity of novel hydrazone-bearing tricyclic quinazolines

Abstract: A series of novel substituted hydrazone-bearing (unsymmetrical azines, RR1C=N–N=CR2R3) tricyclic quinazoline derivatives are reported. All novel compounds were characterized by 1H, 13C nuclear magnetic resonance (NMR), and Fourier-transform infrared (FT-IR) analyses. An important intermediate (E/Z)-hydrazono-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazoline (8) was synthesized from tricyclic quinazoline-4-thione 7 using 80?% of hydrazine hydrate. In addition, the antimicrobial activity of all synthesized novel compounds against three types of pathogenic microorganism was tested, revealing that some compounds showed satisfactory good activity and could serve as lead compounds for further drug discovery and development. Graphical abstract: [Figure not available: see fulltext.].

Copper-Catalyzed Photoinduced Radical Domino Cyclization of Ynamides and Cyanamides: A Unified Entry to Rosettacin, Luotonin A, and Deoxyvasicinone

A general and efficient procedure for the copper-catalyzed photoinduced radical domino cyclization of ynamides and cyanamides providing an efficient access to complex tri-, tetra- and pentacyclic nitrogen heterocycles is reported. Upon visible light irrad

Dual targeting of acetylcholinesterase and tau aggregation: Design, synthesis and evaluation of multifunctional deoxyvasicinone analogues for Alzheimer's disease

Development of multitargeted ligands have demonstrated remarkable efficiency as potential therapeutics for Alzheimer's disease (AD). Herein, we reported a new series of deoxyvasicinone analogues as dual inhibitor of acetylcholinesterase (AChE) and tau aggregation that function as multitargeted ligands for AD. All the multitargeted ligands 11(a-j) and 15(a-g) were designed, synthesized, and validated by 1HNMR, 13CNMR and mass spectrometry. All the synthesized compounds 11(a-j) and 15(a-g) were screened for their ability to inhibit AChE, BACE1, amyloid fibrillation, α-syn aggregation, and tau aggregation. All the screened compounds possessed weak inhibition of BACE-1, Aβ42 and α-syn aggregation. However, several compounds were identified as potential hits in the AChE inhibitory screening assay and cellular tau aggregation screening. Among all compounds, 11f remarkably inhibited AChE activity and cellular tau oligomerization at single-dose screening (10 μM). Moreover, 11f displayed a half-maximal inhibitory concentration (IC50) value of 0.91 ± 0.05 μM and half-maximal effective concentration (EC50) value of 3.83 ± 0.51 μM for the inhibition of AChE and cellular tau oligomerization, respectively. In addition, the neuroprotective effect of 11f was determined in tau-expressing SH-SY5Y cells incubated with Aβ oligomers. These findings highlighted the potential of 11f to function as a multifunctional ligand for the development of promising anti-AD drugs.

Peroxide-Mediated Oxidative Radical Cyclization to the Quinazolinone System: Efficient Syntheses of Deoxyvasicinone, Mackinazolinone and (±)-Leucomidine C

An efficient protocol for obtaining fused quinazolinones through an oxidative free-radical cyclization under metal- and tin-free conditions is described. The oxidative cyclization of various N -3-ω-iodoalkyl derivatives to provide tricyclic systems using dicumyl peroxide as the sole reagent is studied. The method then is employed for the syntheses of 5-, 6-, and 7-membered fused quinazolinone analogues, including the natural products deoxyvasicinone and mackinazolinone. A xanthate-based oxidative radical cascade addition/cyclization process that allows the production of new menthol- and testosterone-quinazolinone conjugates, as well as the first total synthesis of leucomidine C, are also reported.

Redox Condensations of o-Nitrobenzaldehydes with Amines under Mild Conditions: Total Synthesis of the Vasicinone Family

A total synthesis of the vasicinone family of natural products from bulk chemicals was developed. Reductive condensation of o-nitrobenzaldehydes with amines utilizing iron pentacarbonyl as a reducing agent followed by subsequent oxidation leads to a great variety of polycyclic nitrogen-containing heterocycles under mild conditions. Enantiomerically pure vasicinone, rutaecarpine, isaindigotone, and luotonin were synthesized from readily available starting materials like hydroxyproline, nitrobenzaldehyde, pyrrolidine, and piperidine in two to four operational steps without chromatography. The antifungal activity of all products was tested.