700-46-9

Usage

Uses

4-Methylquinazoline is an abdominal sex pheromone in Jewel wasp and other animals.

Synthesis Reference(s)

Journal of the American Chemical Society, 73, p. 5777, 1951 DOI: 10.1021/ja01156a085

InChI:InChI=1/C9H8N2/c1-7-8-4-2-3-5-9(8)11-6-10-7/h2-6H,1H3

Upstream product

• 36926-85-9 quinazolin-4-yl-acetic acid ethyl ester 
• 5257-06-7 N-(2-acetylphenyl)formamide 
• 874497-50-4 2-quinazolin-4-ylmalonic acid diethyl ester 
• 77632-23-6 4'-methyl-ο-<4(3H)-quinazolinylidene>acetophenone 
• 98512-47-1 3-benzoyl-3,4-dihydro-4-methyl-4-quinazolinecarbonitrile 
• 126994-71-6 1,3-dibenzoyl-2,4-dicyano-4-methyl-1,2,3,4-tetrahydroquinazoline 
• 253-82-7 quinazoline 
• 77287-34-4 formamide 
• 7647-01-0 hydrogenchloride 
• 13535-92-7 4-methyl-quinazoline-2-carboxylic acid amide 
• 126994-65-8 2,4-dicyano-1,3-diethoxycarbonyl-1,2,3,4-tetrahydroquinazoline 
• 1239313-35-9 2'-(methyleneamino)acetophenone oxime 
• 67-56-1 methanol 
• 2142-69-0 2-bromophenyl methyl ketone 

Downstream Products

• 101727-73-5 4-(4-nitro-trans-styryl)-quinazoline 
• 106951-39-7 2-quinazolin-4-yl-1-(4-nitro-phenyl)-ethanol 
• 107772-69-0 (E)-4-(4-dimethylaminostyryl)quinazoline 
• 10501-56-1 4-methylquinazoline 3-oxide 
• 26641-42-9 1,6-diisopropylidene-4,4,9,9,9a-pentamethyl-4,4a,9,9a-tetrahydro-bis[1,3]oxazino[3,4-a;3',4'-c]quinazoline-3,8-dione 
• 118925-32-9 1-methyl-4-(3-methyl-3H-benzothiazol-2-ylidenemethyl)-quinazolinium; toluene-4-sulfonate 
• 92736-34-0 1-benzoyl-1,2-dihydro-4-methylquinazoline-2-carbonitrile 
• 6011-26-3 2'-acetylbenzanilide 
• 55-21-0 benzamide 
• 109271-55-8 4-Methyl-1-(4-methyl-benzoyl)-1,2-dihydro-quinazoline-2-carbonitrile 
• 92736-36-2 1-(4-Chloro-benzoyl)-4-methyl-1,2-dihydro-quinazoline-2-carbonitrile 
• 92736-35-1 4-Methyl-1-(4-nitro-benzoyl)-1,2-dihydro-quinazoline-2-carbonitrile 
• 109271-87-6 2-Cyano-4-methyl-2H-quinazoline-1-carboxylic acid phenyl ester 
• 92736-37-3 1-benzoyl-1,2-dihydro-4-methyl-2-<(methylthio)thiocarbonyl>quinazoline-2-carbonitrile 

Relevant academic research and scientific papers

Copper-catalyzed oxidative amination of methanol to access quinazolines

A novel method for the copper-catalyzed oxidative amination of 2′-aminoarylketones with methanol as a C1 carbon source and ammonium acetate as an amine source to construct quinazolines was established in a one-pot manner. The reaction conditions are straightforward and highly atom economic to deliver the corresponding quinazolines in high yields with wide functional group tolerance. Importantly, the present method is applicable on a multigram scale and its synthetic utility is demonstrated by synthesizing quazodine, a muscle-relaxing drug in high yields.

Silver-Catalyzed Isocyanide Insertion into N?H Bond of Ammonia: [5+1] Annulation to Quinazoline Derivatives

A silver-catalyzed [5+1] annulation of o-acylaryl isocyanides with ammonium acetate and hydroxlamine was developed for the efficient and practical synthesis of quinazolines and quinazoline 3-oxides in good to excellent yields, respectively. The domino process involved an unprecedented isocyanide insertion into the N?H bond of ammonia or hydroxylamine and followed by condensation reaction at ambient conditions. (Figure presented.).

Synthesis of Quinazolines via an Iron-Catalyzed Oxidative Amination of N-H Ketimines

An efficient synthesis of quinazolines based on an iron-catalyzed C(sp3)-H oxidation and intramolecular C-N bond formation using tert-BuOOH as the terminal oxidant is described. The reaction of readily available 2-alkylamino benzonitriles with various organometallic reagents led to 2-alkylamino N-H ketimine species. The FeCl2-catalyzed C(sp3)-H oxidation of the alkyl group employing tert-BuOOH followed by intramolecular C-N bond formation and aromatization afforded a wide variety of 2,4-disubstituted quinazolines in good to excellent yields.

An Efficient Three-component, One-pot Synthesis of Quinazolines under Solvent-free and Catalyst-free Condition

An efficient green protocol for the synthesis of quinazolines in the absence of solvent and catalyst has been developed. 2,4-Disubstituted quinazolines have been synthesized from three-component one-pot reactions of 2-aminoaryl ketones, orthoesters, and ammonium acetate. The present method has advantages of operational simplicity, substrate generality, clean reaction, high yields (76-94%), and moderate reaction time. The plausible mechanism of the reaction has been proposed based on the spectral characterization and single crystal X-ray analysis of isolated intermediate.

A novel synthesis of quinazolines by cyclization of 1-(2-isocyanophenyl) alkylideneamines generated by the treatment of 2-(1-azidoalkyl)phenyl isocyanides with NaH

A new and efficient method for the synthesis of quinazolines has been developed. Thus, N-[2-(1-azidoalkyl)phenyl]formamides 1 are dehydrated with POCl3 to give the corresponding 2-(1-azidoalkyl)phenyl isocyanides 2, which are then treated with NaH in DMF at 0° to give quinazolines 6 in satisfactory yields via cyclization of 1-(2-isocyanophenyl)alkylideneamine intermediates 4. This methodology can be applied to the synthesis of the 7-azaanalogs of quinazolines, i.e., pyrido[3,4-d]pyrimidines 9. Copyright

Pd(0)-catalyzed benzylic arylation-oxidation of 4-methylquinazolines via sp3 C-H activation under air conditions

An efficient and selective Pd(0)-catalyzed sp3 C-H bond arylation-oxidation of 4-methylquinazolines is reported. The method enables the introduction of arylketone at the benzylic position of 4-methylquinazolines without the use of an additional directing group, and atmospheric oxygen is used as the sole oxidant.

Copper-catalyzed three-component one-pot synthesis of quinazolines

Two efficient approaches to multi-substituted quinazolines by the three-component one-pot reaction of o-bromo aromatic ketones/aldehydes, ammonia water and aromatic aldehydes, or primary alcohols catalyzed by CuCl have been developed.

An efficient synthesis of quinazolines: a theoretical and experimental study on the photochemistry of oxime derivatives

A new photochemical method for the preparation of quinazolines (2) through irradiation of [2-(methyleneamino)phenyl]methanone oximes (1) is reported. The photoreaction has been studied in depth by experimental, theoretical and photochemical methods. A six-electron electrocyclic ring closure mechanism, followed by water loss, is proposed and rationalized to explain the formation of quinazolines (2).

Behavioural response of Triatoma infestans (Klug) (Hemiptera: Reduviidae) to quinazolines

The behavioural responses of the haematophagous bug Triatoma infestans towards some previously identified components of its faeces: 4-methylquinazoline, 2,4-dimethylquinazoline and their mixtures were evaluated using a video tracking system. Fifth instar nymphs and females but not males were significantly attracted to polyethylene glycol formulations of 4-methyl + 2,4-dimethylquinazoline (50 [μg each). Fifth instar nymphs were also attracted to 4-methylquinazoline alone (50 μg) but females were only attracted by the mixture of both methyl quinazolines (50 μg each). Syntheses of both methyl quinazolines were carried out starting from 2-aminoacetophenone by modifying the conditions of reported procedures.

Palladium complex-catalyzed intermolecular reductive N-heterocyclization: novel synthesis of quinazoline derivatives from 2-nitrobenzaldehyde or 2-nitrophenyl ketones with formamide

A combination of the palladium complex PdCl2(PPh3)2 with MoCl5 shows a high catalytic activity for the intermolecular reductive N-heterocyclization of 2-nitrobenzaldehyde or 2-nitrophenyl ketones with formamide to give the corresponding quinazoline derivatives in moderate yields.For example, in the reaction of 2-nitrobenzaldehyde with formamide, quinazoline was obtained in 46percent yield.We assume that the present reaction proceeds via an active nitrene intermediate which could be generated by selective deoxygenation of nitro group by carbon monoxide.Keywords: Palladium; Molybdenum; Carbon monoxide; Nitrene; Reductive N-heterocyclization