- Access to 2-arylquinazolinesviacatabolism/reconstruction of amino acids with the insertion of dimethyl sulfoxide
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Quinazoline skeletons are synthesized by amino acid catabolism/reconstruction combined with the insertion/cyclization of dimethyl sulfoxide for the first time. The amino acid acts as a carbon and nitrogen source through HI-mediated catabolism and is then reconstructed using aromatic amines and dimethyl sulfoxide (DMSO) as a one-carbon synthon. This protocol is of great significance for the further study of the conversion of amino acids.
- Ma, Jin-Tian,Wang, Li-Sheng,Chai, Zhi,Chen, Xin-Feng,Tang, Bo-Cheng,Chen, Xiang-Long,He, Cai,Wu, Yan-Dong,Wu, An-Xin
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- Palladium-catalyzed carbonylative synthesis of quinazolines: Silane act as better nucleophile than amidine
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A palladium-catalyzed reductive carbonylation reaction has been developed for the synthesis of quinazolines. With N-(2-iodophenyl)benzimidamide as starting materials, a series of quinazolines were obtained through the aromatic aldehyde intermediates in moderate to good yields with good functional group compatibilities. In this system, silane act as better nucleophile than amidine.
- Lu, Jia-Ming,Huo, Yong-Wang,Qi, Xinxin,Wu, Xiao-Feng
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- Nickel-Catalyzed [4 + 2] Annulation of Nitriles and Benzylamines by C-H/N-H Activation
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Nickel-catalyzed [4 + 2] annulation of benzylamines and nitriles via C-H/N-H bond activation, providing straightforward atom-economic access to a wide variety of multisubstituted quinazolines, is reported. Mechanistic investigation revealed that the in situ formed amidines from the coupling of benzylamines and nitriles direct the nickel catalyst to activate the ortho-C-H bond of the phenyl ring of the benzylamine.
- Sikari, Rina,Chakraborty, Gargi,Guin, Amit Kumar,Paul, Nanda D.
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p. 279 - 290
(2021/01/09)
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- Efficient synthesis of quinazolines by the iron-catalyzed acceptorless dehydrogenative coupling of (2-aminophenyl)methanols and benzamides
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The acceptorless dehydrogenation coupling (ADC) of (2-aminophenyl)methanols with benzamides was achieved with catalytic FeCl2·4H2O in an efficient synthesis of quinazolines. This simple catalytic system is atom-economical, environmentally benign and suited to a variety of substrates.
- Zhang, Shi-Qi,Cui, Yao,Guo, Bin,Young, David J.,Xu, Ze,Li, Hong-Xi
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- Dehydrogenative Synthesis of Quinolines, 2-Aminoquinolines, and Quinazolines Using Singlet Diradical Ni(II)-Catalysts
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Simple, straightforward, and atom economic methods for the synthesis of quinolines, 2-aminoquinolines, and quinazolines via biomimetic dehydrogenative condensation/coupling reactions, catalyzed by well-defined inexpensive and easy to prepare singlet diradical Ni(II)-catalysts featuring two antiferromagnetically coupled singlet diradical diamine type ligands are described. Various polysubstituted quinolines, 2-aminoquinolines, and quinazolines were synthesized in moderate to good yields from different low-cost and readily accessible starting materials. Several control experiments were carried out to get insight into the reaction mechanism which shows that the nickel and the coordinated diamine ligands participate in a synergistic way during the dehydrogenation of alcohols.
- Chakraborty, Gargi,Sikari, Rina,Das, Siuli,Mondal, Rakesh,Sinha, Suman,Banerjee, Seemika,Paul, Nanda D.
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p. 2626 - 2641
(2019/02/26)
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- NNN pincer Ru(II)-catalyzed dehydrogenative coupling of 2-aminoarylmethanols with nitriles for the construction of quinazolines
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An efficient NNN pincer Ru(II)-catalyzed preparation of quinazolines via acceptorless dehydrogenative strategy has been developed. Under the optimized conditions, a broad range of substituted o-aminobenzyl alcohols and (hetero)aryl or alkyl nitriles were well tolerated to afford various 2-substituted quinazolines in high yields. Subsequently, a set of control experiments have been performed to elucidate the reaction mechanism, which underwent alcohol oxidation, nitrile hydration, and cyclocondensation steps. The current protocol is featured with several advantages, such as environmental benignity, operational simplicity, broad substrate scope (compatible with aliphatic nitriles, up to 87% yield), and short reaction time (mostly in 2 h).
- Wan, Xiao-Min,Liu, Zi-Lin,Liu, Wan-Qing,Cao, Xiao-Niu,Zhu, Xinju,Zhao, Xue-Mei,Song, Bing,Hao, Xin-Qi,Liu, Guoji
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p. 2697 - 2705
(2019/04/04)
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- Accessing Polysubstituted Quinazolines via Nickel Catalyzed Acceptorless Dehydrogenative Coupling
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Two environmentally benign methods for the synthesis of quinazolines via acceptorless dehydrogenative coupling of 2-aminobenzylamine with benzyl alcohol (Path A) and 2-aminobenzylalcohol with benzonitrile (Path B), catalyzed by cheap, earth abundant and easy to prepare nickel catalysts, containing tetraaza macrocyclic ligands (tetramethyltetraaza[14]annulene (MeTAA) or 6,15-dimethyl-8,17-diphenyltetraaza[14]annulene (MePhTAA)) are reported. A wide variety of substituted quinazolines were synthesized in moderate to high yields starting from cheap and easily available starting precursors. A few control reactions were performed to understand the mechanism and to establish the acceptorless dehydrogenative nature of the catalytic reactions.
- Parua, Seuli,Sikari, Rina,Sinha, Suman,Chakraborty, Gargi,Mondal, Rakesh,Paul, Nanda D.
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p. 11154 - 11166
(2018/09/06)
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- Base-Promoted Synthesis of 2-Aryl Quinazolines from 2-Aminobenzylamines in Water
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A transition-metal-free procedure for the synthesis of a highly valuable class of heteroaromatics, quinazolines, was developed by using easily available 2-aminobenzylamines and α,α,α-trihalotoluenes. The transformation proceeded smoothly in the presence of only sodium hydroxide and molecular oxygen in water at 100 °C, furnishing a variety of 2-aryl quinazolines. The crystallization process of the crude reaction mixture for the purification of the solid products circumvents huge solvent-consuming workup and column chromatographic techniques, which make the overall process more sustainable and economical.
- Chatterjee, Tanmay,Kim, Dong In,Cho, Eun Jin
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p. 7423 - 7430
(2018/07/29)
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- Synthesis of 2-substituted quinazolines by CsOH-mediated direct aerobic oxidative cyclocondensation of 2-aminoarylmethanols with nitriles in air
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By using air as the superior oxidant, a highly atom-efficient synthesis of 2-substituted quinazolines is developed by a CsOH-mediated direct aerobic oxidative reaction of the readily available and stable 2-aminoarylmethanols and nitriles. Effectively working as the promoter in the alcohol oxidation, nitrile hydration, and cyclocondensation steps, CsOH is the best base for the reaction. A similar method can also be extended to the synthesis of substituted quinolines starting from methyl ketones instead of nitriles.
- Yao, Song,Zhou, Kaijing,Wang, Jiabing,Cao, Hongen,Yu, Lei,Wu, Jianzhang,Qiu, Peihong,Xu, Qing
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supporting information
p. 2945 - 2951
(2017/07/24)
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- Copper-Catalyzed Multicomponent Domino Reaction of 2-Bromoaldehydes, Benzylamines, and Sodium Azide for the Assembly of Quinazoline Derivatives
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An efficient three-component domino reaction of 2-bromoaldehydes, benzylamines, and sodium azide has been developed for the synthesis of quinazoline derivatives. This domino process involves copper-catalyzed SNAr, oxidation/cyclization, and denitrogenation sequences. The mild catalytic system enabled the effective construction of three C-N bonds in one operation.
- Xu, Cheng,Jia, Feng-Cheng,Zhou, Zhi-Wen,Zheng, Si-Jie,Li, Han,Wu, An-Xin
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p. 3000 - 3006
(2016/04/26)
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- Lewis acid-catalyzed 2-arylquinazoline formation from: N ′-arylbenzimidamides and paraformaldehyde
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An efficient procedure for the synthesis of 2-arylquinazolines from N′-arylbenzimidamides has been developed under transition-metal-free conditions. In this process, stable and low-toxicity paraformaldehyde was used as the carbon source. A broad range of
- Cheng, Xiufang,Wang, Huamin,Xiao, Fuhong,Deng, Guo-Jun
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supporting information
p. 5773 - 5776
(2016/11/06)
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- A novel ruthenium-catalyzed dehydrogenative synthesis of 2-arylquinazolines from 2-aminoaryl methanols and benzonitriles
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By employing a commercially available Ru3(CO)12/Xantphos/t-BuOK catalyst system, a novel and straightforward ruthenium-catalyzed dehydrogenative synthesis of 2-arylquinazolines has been demonstrated. A series of 2-aminoaryl methanols were efficiently converted in combination with different types of benzonitriles into various desired products in moderate to good yields upon isolation. The synthetic protocol proceeds with the advantages of operational simplicity, high atom efficiency, broad substrate scope, and no need for the use of less environmentally benign halogenated reagents, offering an important basis for accessing 2-arylquinazolines.
- Chen, Mengmeng,Zhang, Min,Xiong, Biao,Tan, Zhenda,Lv, Wan,Jiang, Huanfeng
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supporting information
p. 6028 - 6031
(2015/02/05)
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- One-pot tandem synthesis of 2-arylquinazolines by a multicomponent cyclization reaction
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A series of 2-arylquinazolines have been synthesized in moderate to excellent yields by one-pot tandem reaction of (2-aminophenyl)methanols, aldehydes and ceric ammonium nitrate (CAN). The utility of this transformation was demonstrated by its compatibility with a wide range of functional groups. Thus, the method represents a simple and practical procedure to access 2-arylquinazolines.
- Ye, Leping,Yu, Lin,Zhu, Lijun,Xia, Xiaodong
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p. 13860 - 13869
(2014/01/06)
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- Unexpected copper-catalyzed cascade synthesis of quinazoline derivatives
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The first example of a copper-catalyzed cascade reaction of (2-aminophenyl)methanols with aldehydes using the combination of cerium nitrate hexahydrate and ammonium chloride has been developed, leading to a wide range of 2-substituted quinazolines in moderate to excellent yields. The efficiency of this transformation was demonstrated by compatibility with a wide range of functional groups. Thus, the method represents a convenient and practical strategy for synthesis of 2-substituted quinazoline derivatives.
- Chen, Zhongyan,Chen, Jiuxi,Liu, Miaochang,Ding, Jinchang,Gao, Wenxia,Huang, Xiaobo,Wu, Huayue
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p. 11342 - 11348
(2013/12/04)
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- A cooperative catalytic system of platinum/iridium alloyed nanoclusters and a dimeric catechol derivative: An efficient synthesis of quinazolines through a sequential aerobic oxidative process
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A cooperative catalytic system of heterogeneous polymer-supported bi-metallic platinum/iridium (Pt/Ir) alloyed nanoclusters and 5,5′,6,6′-tetrahydroxy-3,3,3′,3′-tetramethyl-1, 1′-spiro-bisindane (TTSBI) enabled the facile preparation of quinazoline derivatives with low catalyst loadings and broad substrate scope under mild aerobic oxidative conditions. The ability to perform the reaction in gram-scale and under open-air conditions highlights the synthetic application of this cooperative catalytic system. Copyright
- Yuan, Hao,Yoo, Woo-Jin,Miyamura, Hiroyuki,Kobayashi, Shu
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p. 2899 - 2904
(2013/01/15)
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- Enamines; Part. 48 1. 3,4-Dihydroquinazolines from enamines and s ,S-dimethyl-N-( N-arylbenzimidoyl) sulfimides
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Treatment of S,S-dimethyl-N-(N-arylbenzimidoyl)sulfimides with enamines derived from ketones gives 4,4-disubstituted-2-phenyl-3,4-dihydro quinazolines. The reaction involves an 1,3-diaza-1,3-diene intermediate which undergo electrocyclic ring closure to g
- Rossi,Stradi,Visentin
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p. 3581 - 3592
(2007/10/02)
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