31730-65-1Relevant academic research and scientific papers
Heterogeneous selective synthesis of 1,2-dihydro-1,3,5-triazines from alcohols and amidines via Cu/OMS-2-catalyzed multistep oxidation
Meng, Xu,Bi, Xiuru,Wang, Yanmin,Chen, Gexin,Chen, Baohua,Jing, Zhenqiang,Zhao, Peiqing
, p. 34 - 39 (2017)
Copper supported on octahedral manganese oxide molecular sieve (OMS-2) which was obtained via reducing KMnO4 by TBHP was prepared and found to be an efficient catalyst for the synthesis of 1,2-dihydro-1,3,5-triazines directly from alcohols and amidines in one-pot via multistep oxidation. The recyclable heterogeneous catalyst was characterized by BET, XRD, FTIR, TEM and SEM, and the catalytic system can tolerate a wide range of substrates under air with low catalyst loading of supported copper (0.25?mol%), employing OMS-2 as the electron-transfer mediator (ETM) and support.
Tropylium-promoted Ritter reactions
Doan, Son H.,Hussein, Mohanad A.,Nguyen, Thanh Vinh
supporting information, p. 8901 - 8904 (2021/09/10)
The Ritter reaction used to be one of the most powerful synthetic tools to functionalize alcohols and nitriles, providing valuableN-alkyl amide products. However, this reaction has not been frequently used in modern organic synthesis due to its employment of strongly acidic and harsh reaction conditions, which often lead to complicated side reactions. Herein, we report the development of a new method using salts of the tropylium ion to promote the Ritter reaction. This method works well on a range of alcohol and nitrile substrates, giving the corresponding products in good to excellent yields. This reaction protocol is amenable to microwave and continuous flow reactors, offering an attractive opportunity for further applications in organic synthesis.
Copper-Catalyzed Three-Component Cascade Reaction of Benzaldehyde with Benzylamine and Hydroxylamine or Aniline: Synthesis of 1,2,4-Oxadiazoles and Quinazolines
Wang, Chao,Rui, Xiyan,Si, Dongjuan,Dai, Rupeng,Zhu, Yueyue,Wen, Hongmei,Li, Wei,Liu, Jian
supporting information, p. 2825 - 2833 (2021/04/26)
The analogous three-component synthesis strategy for substituted 1,2,4-oxadiazole and quinazoline derivatives from readily available benzaldehyde, benzylamine and hydroxylamine or aniline has been developed. Both the cascade reaction sequences involves nucleophilic addition of C?N bond, introduction a halogen donor, nucleophilic substitution and Cu(II)-catalyzed aerobic oxidation. This synthesis methodology demonstrated good yields, broad substrate scope and oxygen as a green oxidant. Thus, this synthesis protocol provides strategies for the construction of substituted 1,2,4-oxadiazole and quinazolines from readily and simple starting materials. (Figure presented.).
STK19 INHIBITORS FOR TREATMENT OF CANCER
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Paragraph 00417-00418; 00420; 00424-00426, (2020/07/14)
Provided herein are compositions and methods for the treatment and prevention of cancer, including melanoma.
Sulfur-Mediated Decarboxylative Coupling of 2-Nitrobenzyl Alcohols and Arylacetic Acids
Le, Ha V.,Nguyen, Duyen K.,Nguyen, Khang X.,Nguyen, Tung T.,Pham, Phuc H.,Phan, Nam T. S.
supporting information, p. 1112 - 1116 (2020/07/04)
We report a new method for the synthesis of substituted quinazolines by the condensation of 2-nitrobenzyl alcohols with arylacetic acids. The transformation requires the use of urea as a nitrogen source, elemental sulfur as a promoter, DABCO as a base, and DMSO as a solvent. Functionalities such as chloro, fluoro, trifluoromethyl, thienyl, and indolyl groups were all compatible with the reaction conditions. Because our method uses stable simple substrates to obtain the N,N-heterocycles in the absence of transition metals, it offers a potential pathway for preparing complex structures under mild conditions.
Acyl Cyanides as Bifunctional Reagent: Application in Copper-Catalyzed Cyanoamidation and Cyanoesterification Reaction
Chen, Zhengwang,Wen, Xiaowei,Zheng, Weiping,He, Ruolan,Chen, Dou,Cao, Dingsheng,Long, Lipeng,Ye, Min
, p. 5691 - 5701 (2020/04/10)
Cu-catalyzed domino decyanation and cyanation reaction of acyl cyanides with amines or alcohols have been developed. The cyano sources were generated in situ via C-CN cleavage yielding the corresponding cyano substituted amides or esters in moderate to excellent yields. This approach features a cheap copper catalyst, domino decyanation and cyanation reaction, readily available starting materials, broad substrate scope, operational simplicity, and the potential for further transformation of the cyano group.
Visible-Light-Induced Benzylic C-H Functionalization for the Synthesis of 2-Arylquinazolines
Zhang, Jingchang,Wang, Qibao,Guo, Yongen,Ding, Lin,Yan, Maocai,Gu, Yinglin,Shi, Jiajia
supporting information, p. 5934 - 5936 (2019/10/14)
This work reports a mild and efficient approach for the synthesis of substituted quinazolines using 1-(2-aminoaryl)ethan-1-ones in conjunction with arylmethanamines as starting materials via visible-light-induced benzylic C–H functionalization. The reaction proceeded at room temperature with low catalyst loading and the reaction system was clean from beginning to end. Significantly, this method exhibited good tolerance even to free hydroxyl group and amino group contained in substrates.
Synthesis of Quinazolines via an Iron-Catalyzed Oxidative Amination of N-H Ketimines
Chen, Cheng-Yi,He, Fengxian,Tang, Guangrong,Yuan, Huiqing,Li, Ning,Wang, Jinmin,Faessler, Roger
, p. 2395 - 2401 (2018/02/23)
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.
Copper-Catalyzed Synthesis of Substituted Quinazolines from Benzonitriles and 2-Ethynylanilines via Carbon-Carbon Bond Cleavage Using Molecular Oxygen
Wang, Xu,He, Dandan,Huang, Yubing,Fan, Qihang,Wu, Wanqing,Jiang, Huanfeng
, p. 5458 - 5466 (2018/05/28)
A copper-catalyzed process for the synthesis of substituted quinazolines from benzonitriles and 2-ethynylanilines using molecular oxygen (O2) as sole oxidant is described. The mild catalytic system enabled the effective cleavage of the C-C triple bond and construction of new C-N and C-C bonds in one operation. Furthermore, the compound N,N-dimethyl-4-(2-(4-(trifluoromethyl)phenyl)quinazolin-4-yl)aniline (3dj) exhibited obvious aggregation-induced emission phenomenon, and the fluorescence quantum yield (ΦF,film) and lifetime (τfilm) were measured to be 45.5% and 5.8 ns in thin films state, respectively.
Lewis-Acid-Catalysed Activation of Nitriles: A Microwave-Assisted Solvent-Free Synthesis of 2,4-Disubstituted Quinazolines and 1,3-Diazaspiro[5.5]undec-1-enes
Saikia, Ujwal Pratim,Borah, Geetika,Pahari, Pallab
supporting information, p. 1211 - 1217 (2018/03/21)
Two different modes of cyclization take place to synthesize quinazoline, quinazolinone, and 1,3-diazaspiro[5.5]undec-1-ene derivatives through the Lewis-acid-catalysed activation of both aliphatic and aromatic nitriles in a single-step, solvent-free, and transition-metal-free reaction. An amidine is expected to form as an intermediate; this then undergoes intramolecular cyclization in a one-pot reaction sequence. The reaction is carried out under microwave irradiation using trimethylsilyltrifluoromethane sulfonate (TMSOTf) as a catalyst and nitriles as a nitrogen source with the respective reaction partners.
