1859-77-4Relevant academic research and scientific papers
Method for synthesizing 2-aminobenzophenone compound
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Paragraph 0083-0085, (2019/02/04)
The invention discloses a method for synthesizing a 2-aminobenzophenone compound, and belongs to the technical field of organic synthesis. According to the key point of the technical scheme, the method comprises the following steps that an N-nitroso-2-ami
An Efficient Metal-Free Method for the Denitrosation of Aryl N-Nitrosamines at Room Temperature
Chaudhary, Priyanka,Korde, Rishi,Gupta, Surabhi,Sureshbabu, Popuri,Sabiah, Shahulhameed,Kandasamy, Jeyakumar
supporting information, p. 556 - 561 (2017/11/13)
A simple and practical method for the denitrosation of aryl N-nitrosamines to secondary amines is reported under metal-free conditions using iodine and triethylsilane. Several reduction-susceptible functional groups such as alkene, alkyne, nitrile, nitro, aldehyde, ketone and ester were found to be very stable during the denitrosation, which is remarkable. Broad substrate scope, room temperature reactions and excellent yields are the additional features of the current methodology. (Figure presented.).
Synthesis of 2-aminobenzophenones through acylation of anilines with α-oxocarboxylic acids assisted by: Tert -butyl nitrite
Wang, Qianqian,Zhang, Xinying,Fan, Xuesen
, p. 7737 - 7747 (2018/11/02)
In this paper, a regioselective, efficient and convenient synthesis of 2-aminobenzophenones through acylation of anilines with α-oxocarboxylic acids assisted by tert-butyl nitrite is presented. Interestingly, tert-butyl nitrite acts as not only an efficient and mild nitrosation reagent, but also a sustainable oxidant required in the Pd(ii)-catalyzed decarboxylative acylation. Meanwhile, the NO unit turned out to be an easily introduced and readily removable directing group for the regioselective acylation.
Transition-Metal-Free Synthesis of Acridones via Base-Mediated Intramolecular Oxidative C?H Amination
Wei, Wen-Tao,Sheng, Jian-Fei,Miao, Hui,Luo, Xiang,Song, Xian-Heng,Yan, Ming,Zou, Yong
supporting information, p. 2101 - 2106 (2018/06/14)
Intramolecular oxidative C?H amination of 2-aminobenzophenones was achieved in the presence of potassium tert-butoxide and dimethyl sulfoxide. A series of functionalized acridones were prepared in moderate to excellent yields in a mild, efficient, and transition-metal-free manner. (Figure presented.).
Palladium-catalyzed oxidative C-H bond acylation of N-nitrosoanilines with toluene derivatives: A traceless approach to synthesize N-alkyl-2-aminobenzophenones
Wu, Yinuo,Feng, Ling-Jun,Lu, Xiao,Kwong, Fuk Yee,Luo, Hai-Bin
, p. 15352 - 15354 (2015/01/08)
A palladium-catalyzed cascade cross-coupling of N-nitroso-anilines and toluene derivatives for the direct synthesis of N-alkyl-2-aminobenzophenones is described. N-nitroso groups in anilines can act as the traceless directing groups while toluene derivatives can serve as effective acyl precursors under mild reaction conditions.
A novel intramolecular photocyclization of N-(2-bromoalkanoyl) derivatives of 2-acylanilines via 1,8-hydrogen abstraction
Nishio, Takehiko,Koyama, Hiroyuki,Sasaki, Daigo,Sakamoto, Masami
, p. 996 - 1003 (2007/10/03)
The photochemical reactions of different N-(2-acylphenyl)-2-bromo-2- methylpropanamides have been investigated. Irradiation of the N-unsubstituted anilides 1a-1c gave the corresponding dehydrobromination, cyclization, and bromo-migration products 2, 3, and 4, respectively (Table 1). Irradiation of the N-alkyl anilides 1e-1g afforded the corresponding deacylation and cyclization products 5 and 6, respectively, whereas irradiation of the N-alkyl anilides 1i-1k, carrying 2-benzoyl groups on the aromatic rings, afforded the unexpected tricyclic lactams 7 (besides 2, 5, and 6). The formation of the cyclization products 6 could be rationalized in terms of an electrocyclic ring closure of the 6π-electron-conjugated enamides 2 produced by dehydrobromination of 1, followed by thermal 1,5-acyl migration (Path B in the Scheme). The formation of the bridged lactams 7 probably follows a mechanism involving the 1,7-diradical 8 generated by ζ-H-abstraction (1.8-H transfer) by an excited acyl O-atom (Path A).
Photo-Fries rearrangement of N-arylsulfonamides to aminoaryl sulfone derivatives
Park, Kwanghee Koh,Lee, Jin Joo,Ryu, Jaegyung
, p. 7651 - 7659 (2007/10/03)
Photochemical reaction of variously substituted p-toluenesulfonanilides was studied. The reaction gives rearranged products, o- and p-amino-substituted diaryl sulfones with the combined yields of 38-72%: the p-isomer is more favored over the o-isomer with the selectivity ratio of 1.1-4.3 depending on the substituents. N-Alkylation of the sulfonanilides increases the yields of the rearranged products, and e-withdrawing substituents on the N-phenyl ring does not lower the yields drastically. This study provides simple methodology for the synthesis of o- and p-aminoaryl sulfones which are otherwise not easily accessible.
Tetrazoles: XLVI. 3H-1,3,4-benzo-and pyrido[6,7-b][1,3,4]triazepines from 5-aryltetrazoles. Synthesis and chemical properties
Nikulin,Artamonova,Koldobskii
, p. 1525 - 1529 (2007/10/03)
2,5-Disubstituted 3H-1,3,4-benzotriazepines were synthesized by heating of N-imidoyltetrazoles in toluene at 110°C. Alkylation of these compounds, as well as of 3H-pyrido[6,7-b][1,3,4]triazepines with alkyl halides in THF in the presence of potassium tert-butoxide gave the corresponding 1-alkyl derivatives in good yield and with high regioselectivity.
Carbon Dioxide: A Reagent for the Simultaneous Protection of Nucleophilic Centres and the Activation of Alternative Locations to Electrophilic Attack. Prt III. A New Synthetic Method for the ortho-Substitution of N-Monoalkylanilines
Katritzky, Alan R.,Fan, Wei-Qiang,Akutagawa, Kunihiko
, p. 4027 - 4034 (2007/10/02)
N-Methyl- and N-ethyl-aniline are regiospecifically converted into a range of ortho-substituted derivatives, using carbon dioxide both for N-protection and as an intermediate carbanion stabilizing group, and t-butyllithium to lithiate the ortho-carbon atom.The rersulting lithium N-(ortho-substituted-phenyl)-N-methyl- and -N-ethylcarbamates undergo smooth acid-catalysed decarboxylation under mild conditions.No alpha-substituted products were detected.
