23465-73-8Relevant academic research and scientific papers
B(C6F5)3-Catalyzed Deoxygenative Reduction of Amides to Amines with Ammonia Borane
Pan, Yixiao,Luo, Zhenli,Han, Jiahong,Xu, Xin,Chen, Changjun,Zhao, Haoqiang,Xu, Lijin,Fan, Qinghua,Xiao, Jianliang
, p. 2301 - 2308 (2019/01/30)
The first B(C6F5)3-catalyzed deoxygenative reduction of amides into the corresponding amines with readily accessible and stable ammonia borane (AB) as a reducing agent under mild reaction conditions is reported. This metal-free protocol provides facile access to a wide range of structurally diverse amine products in good to excellent yields, and various functional groups including those that are reduction-sensitive were well tolerated. This new method is also applicable to chiral amide substrates without erosion of the enantiomeric purity. The role of BF3 ? OEt2 co-catalyst in this reaction is to activate the amide carbonyl group via the in situ formation of an amide-boron adduct. (Figure presented.).
Metal-free tandem cyclization/hydrosilylation to construct tetrahydroquinoxalines
Pan, Yixiao,Chen, Changjun,Xu, Xin,Zhao, Haoqiang,Han, Jiahong,Li, Huanrong,Xu, Lijin,Fan, Qinghua,Xiao, Jianliang
supporting information, p. 403 - 411 (2018/02/07)
A one-pot tandem procedure involving cyclization and sequential hydrosilylation of imines and amides under the catalysis of B(C6F5)3 has been developed for the step-economical construction of 1,2,3,4-tetrahydroquinoxalines directly from readily available 1,2-diaminobenzenes, α-ketoesters and low-cost, safe polymethylhydrosiloxane (PMHS). This metal-free approach provides various products in good to excellent yields, and displays a wide range of substrate scope and a high degree of functional group tolerance even to reduction-sensitive moieties. The choice of hydrosilanes is critical to the catalysis, and PMHS has proved to be optimal. Decreasing the amount of PMHS could enable the reaction to stop at the 3,4-dihydroquinoxalin-2(1H)-one stage. The procedure is convenient and scalable, and neither a dried solvent nor an inert atmosphere is required. Moreover, the enantioselective construction of these products was explored, and promising results were achieved.
Synthesis of 9,10-substituted 3,4,10,10a-tetrahydro-2H,9H-1-oxa-4a,9- diazaphenanthrenes by reductive cyclization method
Rajachandrasekhar,Hariprasad,Venugopala Rao,Venkataiah,Dubey
, p. 3161 - 3165 (2014/07/22)
Commercially available o-phenylenediamine (1) was treated with methyl α-bromo-α-aryl acetate to obtain 3-aryl-3,4-dihydro-1Hquinoxalin- 2-one (2). The latter was reacted with benzyl bromide to obtain 4-benzyl-3-aryl-3,4-dihydro-1H-quinoxalin-2-one (3). Tr
FUSED TETRACYCLIC PYRIDO[4,3-B]INDOLE AND PYRIDO[3,4-B]ONDOLE DERIVATIVES AND METHODS OF USE
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Page/Page column 236, (2011/09/19)
This disclosure is directed to fused tetracyclic pyrido[4,3-b]indoles and pyrido[3,4- b]indoles. Pharmaceutical compositions comprising the compounds are also provided, as are methods of using the compounds in a variety of therapeutic applications, including the treatment of a cognitive disorder, psychotic disorder, neurotransmitter-mediated disorder and/or a neuronal disorder.
Synthetic studies of bioactive quinoxalinones: A facile approach to potent euglycemic and hypolipidemic agents
Kamila, Sukanta,Biehl, Edward R.
, p. 1931 - 1939 (2007/10/03)
Substituted quinoxalin-2-ones have been prepared in high yields in a one-pot reaction in which a 1:1 mixture of 1,2-diaminobenzene and appropriate ethyl 2-bromoalkyl/aryl acetate is subjected to microwave irradiation in presence of DBU at 190 °C for 6 min
Formal hydride transfer mechanism for photoreduction of 3-phenylquinoxalin-2-ones by amines. Association of 3-phenylquinoxalin-2-one with aliphatic amines
De la Fuente,Canete,Zanocco,Saitz,Jullian
, p. 7949 - 7958 (2007/10/03)
The photophysical and photochemical behavior of 1-methyl-3-phenylquinoxalin-2-one (MeNQ) and 3-phenylquinoxalin-2-one (HNQ) in the presence of amines is reported. While HNQ fluorescence shows an auxochromic effect and a bathochromic shift with added amine
Photochemical Reactions of Quinoxalin-2-ones and Related Compounds
Nishio, Takehiko
, p. 565 - 570 (2007/10/02)
Irradiation of the quinoxalin-2-ones (1a-c, e-g and i) in the presence of amines gave reductive dimers, the dihydro dimers (3a-c, e-g and i) of quinoxalin-2-ones, while irradiation of the quinoxalin-2-ones (1d, h and j), which possess a phenyl group at th
SYNTHESIS AND REACTIONS OF 3-PHENYL-3,4-DIHYDRO-1,4-QUINOXALIN-2(1H)-ONE AND ITS HETEROCYCLIC ANALOGUES
Olagbemiro, T.O.,Nyakutse, C.A.,Lajide, L.,Agho, M.O.,Chukwu, C.E.
, p. 473 - 480 (2007/10/02)
The lactams quinoxalinone 3a, benzothiazinone 3b and benzothiazinone 3c were synthesized by reactions of methyl 2-bromo-2-phenylethanoate 1 with orthosubstituted arylamines 2a-2c.Subsequent reductive alkylation of the lactams with sodium hydride and iodom
