- Copper-catalyzed oxidative amination of methanol to access quinazolines
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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.
- Satish, Gandhesiri,Polu, Ashok,Kota, Laxman,Ilangovan, Andivelu
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p. 4774 - 4782
(2019/05/24)
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- Silver-Catalyzed Isocyanide Insertion into N?H Bond of Ammonia: [5+1] Annulation to Quinazoline Derivatives
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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.).
- Zhang, Lingjuan,Li, Juanjuan,Hu, Zhongyan,Dong, Jinhuan,Zhang, Xian-Ming,Xu, Xianxiu
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supporting information
p. 1938 - 1942
(2018/04/02)
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- Synthesis of Quinazolines via an Iron-Catalyzed Oxidative Amination of N-H Ketimines
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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.
- Chen, Cheng-Yi,He, Fengxian,Tang, Guangrong,Yuan, Huiqing,Li, Ning,Wang, Jinmin,Faessler, Roger
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p. 2395 - 2401
(2018/02/23)
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- An Efficient Three-component, One-pot Synthesis of Quinazolines under Solvent-free and Catalyst-free Condition
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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.
- Bhat, Subrahmanya Ishwar,Das,Trivedi, Darshak R.
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p. 1253 - 1259
(2015/08/06)
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- A novel synthesis of quinazolines by cyclization of 1-(2-isocyanophenyl) alkylideneamines generated by the treatment of 2-(1-azidoalkyl)phenyl isocyanides with NaH
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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
- Ezaki, Kosuke,Kobayashi, Kazuhiro
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p. 822 - 829
(2014/07/07)
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- Pd(0)-catalyzed benzylic arylation-oxidation of 4-methylquinazolines via sp3 C-H activation under air conditions
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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.
- Zhao, Dan,Zhu, Min-Xue,Wang, Yue,Shen, Qi,Li, Jian-Xin
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p. 6246 - 6249
(2013/09/23)
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- Copper-catalyzed three-component one-pot synthesis of quinazolines
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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.
- Ju, Jia,Hua, Ruimao,Su, Ji
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p. 9364 - 9370
(2012/11/07)
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- An efficient synthesis of quinazolines: a theoretical and experimental study on the photochemistry of oxime derivatives
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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).
- Alonso, Rafael,Caballero, Alegría,Campos, Pedro J.,Sampedro, Diego,Rodríguez, Miguel A.
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supporting information; experimental part
p. 4469 - 4473
(2010/07/08)
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- Behavioural response of Triatoma infestans (Klug) (Hemiptera: Reduviidae) to quinazolines
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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.
- Alzogaray,Fontan,Camps,Masuh,Santo Orihuela,Fernandez,Cork,Zerba
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p. 1190 - 1196
(2007/10/03)
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- Palladium complex-catalyzed intermolecular reductive N-heterocyclization: novel synthesis of quinazoline derivatives from 2-nitrobenzaldehyde or 2-nitrophenyl ketones with formamide
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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
- Akazome, Motohiro,Yamamoto, Jun,Kondo, Teruyuki,Watanabe, Yoshihisa
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p. 229 - 234
(2007/10/02)
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- Reissert Compound Studies. LXI. Preparation and Reactions of Quinazoline Di-Reissert Compounds
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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.
- Hahn, Jung-Tai,Popp, Frank D.
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p. 1357 - 1372
(2007/10/02)
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- o-Aminophenyl Alkyl/Aralkyl Ketones and Their Derivatives: Part V -- An Efficient Synthetic Route to Some Biologically Active 4-Substituted Quinazolines
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4-Substituted quinazolines (II) have been prepared by the action of formamide on o-aminophenyl alkyl and aralkyl ketones (I) in the presence of borontrifluoride etherate as catalyst, and tested for their inotropic activity.
- Byford, A.,Goadby, P.,Hooper, M.,Kamath, H. V.,Kulkarni, Sheshgiri N.
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p. 396 - 397
(2007/10/02)
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- EXTRUSION REACTIONS-VIII. A FACILE SYNTHESIS OF 4-ALKYL QUINAZOLINES AND 1-METHYL-2-ARYL-4-QUINOLONES
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With aq. sodium hydroxide, ο-acetophenones 4b (R'=H, R=Ar) or ο-(4-quinazolinyl)acetophenones 4a (R'=Me, Et; R=Ar) provide 4-alkylquinazolines 6 but 1-methyl-4-phenacyl or phenacylidene-3H-quinazolinium derivatives 10a or 10b give N-methyl-4-quinolone derivatives 11.
- Singh, Harjit,Aggarwal, Sunil K.,Malhotra, Nageshwar
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p. 1139 - 1144
(2007/10/02)
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- STUDIES WITH REISSERT COMPOUNDS. PART 17. MONO-REISSERT COMPOUND FORMATION AT THE 1,2-POSITION OF THE QUINAZOLINE SYSTEM.
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4-Substituted quinazolines have been selectively converted into mono-Reissert compounds at the 1,2-position by use of acid chlorides and trimethylsilyl cyanide.Various reactions of the quinazoline Reissert compounds are reported.For example, conjugate base generation at the 2-position leads to a 1,2-rearrangement, whereas substitution occurs in the presence of an alkyl halide, providing, after hydrolysis, 2-alkyl-4-phenylquinazolines in good yield.Ring annellation by intramolecular alkylation is also reported.The quinazoline Reissert compound conjugate base reacts with aldehydes to give alcohol esters which can further be converted, via the alcohol and use of phosgene, to novel oxazoloquinazoline derivatives.
- Uff, Barrie C.,Joshi, Bijaya L.,Popp, Frank D.
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p. 2295 - 2304
(2007/10/02)
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- Preparation and Reactions of Mono-Reissert Compounds and Analogs at the 3,4-Position of Quinazoline
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Quinazoline, acid chlorides, and trimethylsilyl cyanide have been converted to mono-Reissert compounds at the 3,4-position of the quinazoline system.Various reactions of these quinazoline Reissert compounds are reported.
- Kant, Joydeep,Popp, Frank D.,Uff, Barrie C.
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p. 1313 - 1316
(2007/10/02)
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- Reactions of the Anion of Quinazoline Reissert Compound (3-Benzoyl-3,4-dihydro-4-quinazolinecarbonitrile) with Electrophiles
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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
- Higashino, Takeo,Kokubo, Hiroyasu,Hayashi, Eisaku
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p. 950 - 961
(2007/10/02)
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- Substituted pyrrolo [1,2-c] quinazolines and pharmaceutical compositions and methods employing them
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Substituted pyrrolo[1,2-c] quinazolines useful for their cardiovascular activities and as antiasthmatic agents.
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