36082-71-0

Basic information

• Product Name: QUINAZOLINE-4-CARBONITRILE
• Synonyms: QUINAZOLINE-4-CARBONITRILE;4-Cyanoquinazoline
• CAS NO: 36082-71-0
• Molecular Formula: C₉H₅N₃
• Molecular Weight: 155.16
• Mol File: 36082-71-0.mol

Chemical Properties

• Boiling Point: 334.1°C at 760 mmHg
• Flash Point: 118.1°C
• Appearance: /
• Density: 1.29g/cm³
• Vapor Pressure: 0.000131mmHg at 25°C
• Refractive Index: 1.662
• CAS DataBase Reference: QUINAZOLINE-4-CARBONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: QUINAZOLINE-4-CARBONITRILE(36082-71-0)
• EPA Substance Registry System: QUINAZOLINE-4-CARBONITRILE(36082-71-0)

Safety Data

• Hazardous Substances Data: 36082-71-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
QUINAZOLINE-4-CARBONITRILE is used as a building block for the synthesis of biologically active compounds due to its unique quinazoline ring system and carbonitrile functional group. It plays a crucial role in the development of potential therapeutic agents, contributing to the creation of new medicines with diverse pharmacological properties.
Used in Drug Discovery and Development:
As an intermediate in the synthesis of various pharmaceuticals, QUINAZOLINE-4-CARBONITRILE is utilized for its potential to enhance the properties of drug candidates, making it a valuable component in the advancement of novel treatments and therapies.
Used in Organic Synthesis and Chemical Research:
Beyond its pharmaceutical applications, QUINAZOLINE-4-CARBONITRILE is also employed in organic synthesis and chemical research, where its distinctive structure allows for the exploration of new chemical reactions and the development of innovative synthetic pathways.

InChI:InChI=1/C9H5N3/c10-5-9-7-3-1-2-4-8(7)11-6-12-9/h1-4,6H

Upstream product

• 92736-32-8 3-benzoyl-3,4-dihydro-4-quinazolinecarbonitrile 
• 151-50-8 potassium cyanide 
• 99933-56-9 (4-Nitro-phenyl)-quinazolin-4-yl-methanone 
• 100-52-7 benzaldehyde 
• 76051-72-4 2,4-dicyano-1,3-dibenzoyl-1,2,3,4-tetrahydroquinazoline 
• 99933-48-9 Benzoic acid cyano-phenyl-quinazolin-4-yl-methyl ester 
• 99933-49-0 Benzoic acid (4-chloro-phenyl)-cyano-quinazolin-4-yl-methyl ester 
• 99933-51-4 Benzoic acid cyano-(4-nitro-phenyl)-quinazolin-4-yl-methyl ester 
• 99933-52-5 Benzoic acid cyano-(3-nitro-phenyl)-quinazolin-4-yl-methyl ester 
• 187336-04-5 4-(α-benzyl-α-hydroxybenzyl)quinazoline 
• 187336-14-7 1-(4-methoxyphenyl)-2-phenyl-1-(quinazoline-4-yl)ethanol 
• 187336-15-8 (4-Methoxy-phenyl)-phenyl-quinazolin-4-yl-methanol 
• 187336-13-6 1-(4-Chloro-phenyl)-2-phenyl-1-quinazolin-4-yl-ethanol 

Relevant articles and documents

Carbon-carbon bond cleavage of α-hydroxybenzylheteroarenes catalyzed by cyanide ion: Retro-benzoin condensation affords ketones and heteroarenes and benzyl migration affords benzylheteroarenes and arenecarbaldehydes

4-(α-Benzylα-hydroxybenzyl)quinazoline (4a) underwent retro-benzoin condensation catalyzed by cyanide ion to give deoxybenzoin (2a) and quinazoline (5a). Similarly, several nitrogen-containing heteroarenes (4, 9, 12, 16-19) having an α-hydroxybenzyl group at the α-position of the nitrogen underwent retro-benzoin type condensation to afford kelones (2) and heteroarenes (5). However, similar reaction of pyrazolopyrimidines (13, 14, 15) having an α-benzyl-α-hydroxybelzyl group resulted in benzyl migration, giving benzylpyrazolopyrimidines (8) and arenecarbaldehydes (3). Tetrabutylammonium cyanide (11, Bu4NCN) was a more effective cyanide ion donor than KCN (10). The retro-benzoin condensation was applied to the synthesis of 2-substituted quinazolines (38) from 2-chloro-4- aroylquinazolines (34), using the aroyl group as a protecting and electron- withdrawing group.

Carbon-carbon bond cleavage of α-hydroxybenzyl-heteroarenes to ketones and heteroarenes by catalytic action of cyanide ion based on retrobenzoin condensation

Treatment of 4-(α-benzyl-α-hydroxybenzyl)quinazoline (2a) with potassium cyanide in DMF resulted in carbon-carbon bond cleavage to give benzyl phenyl ketone (3a) and quinazoline (4). Similar results were obtained with other 4-(α-hydroxybenzyl)quinazolines (2b-f and 7a). This reaction proceeds through retrobenzoin condensation. This condensation also proceeded in pyrazolopyrimidine (9a) triazolopyrimidine (10a), quinoxaline (11a), and benzimidazole (12a), and the imidazolium salt (16) was an effective catalyst.

Reissert Compound Studies. LXI. Preparation and Reactions of Quinazoline Di-Reissert Compounds

Various di-Reissert compounds and analogs were prepared from quinazoline by use of trimethylsilyl cyanide together with a catalytic amount of anhydrous aluminum chloride.Reactions of these quinazoline di-Reissert compounds are reported.

Reactions of the Anion of Quinazoline Reissert Compound (3-Benzoyl-3,4-dihydro-4-quinazolinecarbonitrile) with Electrophiles

Reactions of the quinazoline Reissert compound (2) with various electrophiles in the presence of sodium hydride in N,N-dimethylformamide were investigated.The reactions with aldehydes (3) and ketones (12) gave α-aryl (or alkyl)-(7) and α-alkyl-α-aryl (or alkyl)-4-quinazolinylmethyl benzoates (16), respectively.The reaction with ?-deficient heteroaromatics (10a-c) gave 4-heteroarylquinazolines (20a-c).Alkylation (or arylation) with alkyl (or aryl) halides (23a-c) afforded 4-substituted 3-benzoyl-3,4-dihydro-4-quinazolinecarbonitriles (24a-c).The reaction with dimethyl acetylenedicarboxylate proceeded in two ways, giving dimethyl 3-phenylpyrroloquinazoline-1,2-dicarboxylate (27) and dimethyl 3-benzoyl-4-cyano-1,2,3,4-tetrahydro-2,4-ethenoquinazoline-9,10-dicarboxylate (28).The reaction with 2-alkenonitriles (29a,b) resulted in the formation of 2-benzoyl-3-(4-quinanolinyl)alkanonitriles (32a,b).Keywords - rearrangement; substitution; 1,3-dipolar addition; quinazoline Reissert compound anion; α-substituted 4-quinazolinylmethyl benzoate; 4-heteroarylquinazoline; 4-substituted 3,4-dihydro-4-quinazoline carbonitrile; pyrroloquinazoline; 2,4-ethenoquinazoline; 2-benzoyl-3-(4-quinazolinyl)alkanonitrile

Reaction of 4-Aroylquinazolines with Sodium Hydroxide: Aryl Migration to Give 4-Aryl-3,4-dihydro-4-quinazolinecarboxylic Acids and Formation of Quinazoline and Aroic Acids

4-Aroylquinazolines (3) were prepared in good yields by alkaline hydrolysis of α-aryl-4-quinazolinylmethyl benzoates (15), followed by oxidation.The reaction of 3 with sodium hydroxide in dimethyl sulfoxide(DMSO) was found to proceed in two ways.One path is the aryl migration to lead to 4-aryl-3,4-dihydro-4-quinazolinecarboxylic acids (4), and the other is the fission of the C4-CO bond to yield quinazoline (5) and aroic acids (6). Potassium ferricyanide oxidized the carboxylic acids 4 to the corresponding 4-arylquinazolines (14) with elimination of carbon dioxide. Reaction of 4-benzoylquinazoline (3a) with methylmagnesium iodide did not result in the migration, but instead yielded of α-methyl-α-phenyl-4-quinazolinemethanol (18) and 3,4-dihydro-α,4-dimethyl-α-phenyl-4-quinazolinemethanol (19).

Preparation and Reactions of Quinazoline Reissert Compound (3-Benzoyl-3,4-dihydro-4-quinazolinecarbonitrile)

The benzoylation of 3,4-dihydro-4-quinazolinecarbonitrile (3) with benzoyl chloride in pyridine gave quinazoline Reissert compound (1, 3-benzoyl-3,4-dihydro-4-quinazolinecarbonitrile) in 82percent yield. The alkaline hydrolysis of 1 in methanol resulted in the formation of quinazoline (2) and benzoic acid (4).Acid hydrolysis gave 2-benzamido-2-(2-aminophenyl)acetonitrile (6), 4, and 2.The HCl salt of 1 existed predominantly in the cyclic amidinium structure of the type 8.Compound 1reacted with sodium hydride in dimethylformamide to yield 4-quinazolinecarbonitrile (9), α-phenyl-4-quinazolinylmethyl benzoate (10) and O-benzoylbenzoin (11). In the present paper we compare the chemical properties of 1 with those of isoquinoline Reissert compound (13, 2-benzoyl-1,2-dihydro-1-isoquinolinecarbonitrile). Keywords --- quinazoline Reissert compound; cyclic amidinium cation; alkaline hydrolysis; acid hydrolysis; quinazoline Reissert compound anion; acetonitrile derivative; 4-quinazolinecarbonitrile; 4-quinazolinylmethyl benzoate derivative