1859-76-3Relevant academic research and scientific papers
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 (2003)
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.
Nickel/Photo-Cocatalyzed Asymmetric Acyl-Carbamoylation of Alkenes
Fan, Pei,Lan, Yun,Zhang, Chang,Wang, Chuan
, p. 2180 - 2186 (2020/03/03)
An unprecedented asymmetric acyl-carbamoylation of pendant alkenes tethered on aryl carbamic chlorides with both aliphatic and aromatic aldehydes has been developed via the cooperative catalysis of a chiral nickel-PHOX complex and tetrabutylammonium decatungstate. This reaction represents the first example of merging hydrogen-atom-transfer photochemistry and asymmetric transition metal catalysis in difunctionalization of alkenes. Using this protocol, a variety of oxindoles bearing a challenging quaternary stereogenic center are furnished under mild conditions in highly enantioselective manner.
Method for synthesizing 2-aminobenzophenone compound
-
Paragraph 0016-0021; 0024-0035; 0037-0039; 0040-0043, (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
Method for synthesizing ortho-amino aromatic ketone from aromatic carboxylic acid
-
Paragraph 0059; 0060, (2019/07/04)
Disclosed is a method for synthesizing ortho-amino aromatic ketone from aromatic carboxylic acid. The method comprises the steps that with 2-arylsulfonamido aromatic carboxylic acid shown in the description as a raw material and triphenylphosphine as a deoxidizer, under the illumination of blue light, in a 1,4-dioxane solution, under an argon atmosphere, in the presence of the dipotassium hydrogenphosphate, with [Ir(dF(CF3)ppy)2(dtbbpy)]PF6 as a photocatalyst, the ortho-amino aromatic ketone compound is obtained; the structure of the photocatalyst [Ir(dF(CF3)ppy)2(dtbbpy)]PF6 is shown in thedescription.
Deoxygenative Arylation of Carboxylic Acids by Aryl Migration
Ruzi, Rehanguli,Ma, Junyang,Yuan, Xiang-Ai,Wang, Wenliang,Wang, Shanshan,Zhang, Muliang,Dai, Jie,Xie, Jin,Zhu, Chengjian
supporting information, p. 12724 - 12729 (2019/11/05)
An unprecedented deoxygenative arylation of aromatic carboxylic acids has been achieved, allowing the construction of an enhanced library of unsymmetrical diaryl ketones. The synergistic photoredox catalysis and phosphoranyl radical chemistry allows for precise cleavage of a stronger C?O bond and formation of a weaker C?C bond by 1,5-aryl migration under mild reaction conditions. This new protocol is independent of substrate redox-potential, electronic, and substituent effects. It affords a general and promising access to 60 examples of synthetically versatile o-amino and o-hydroxy diaryl ketones under redox-neutral conditions. Furthermore, it also brings one concise route to the total synthesis of quinolone alkaloid, (±)-yaequinolone A2, and a viridicatin derivative in satisfying yields.
Palladacycle-Phosphine Catalyzed Methylation of Amines and Ketones Using Methanol
Mamidala, Ramesh,Biswal, Priyabrata,Subramani, M. Siva,Samser, Shaikh,Venkatasubbaiah, Krishnan
, p. 10472 - 10480 (2019/08/20)
Methylation of amines and ketones with palladacycle precatalyst has been performed using methanol as an environmentally benign reagent. Various ketones and amines undergo methylation reaction to yield monomethylated amines or ketones in moderate to good isolated yields. Moreover, this protocol was tested for the chemoselective methylation of 4-aminobenzenesulfonamide. The scope of the reaction was further extended to the deuteromethylation of ketones.
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.).
Selective N-monomethylation of primary anilines with dimethyl carbonate in continuous flow
Seo, Hyowon,Bédard, Anne-Catherine,Chen, Willie P.,Hicklin, Robert W.,Alabugin, Alexander,Jamison, Timothy F.
, p. 3124 - 3128 (2017/12/11)
Selective N-monomethylation of anilines has been achieved under continuous flow conditions using dimethyl carbonate as a green methylating agent in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene. Our methodology takes advantage of the expanded process windows available in the continuous flow regime to safely induce monomethylation in superheated solvents at high pressure. We propose selective N-monomethylation is achieved via an in situ protection-deprotection pathway, which is supported by the observed reactivities of several putative reaction intermediates. The robust and scalable method was applicable to a broad range of primary aniline substrates including ortho-, meta-, and para-substituted anilines, as well as electron-rich and electron-deficient anilines. The synthetic precursor of diazepam, 5-chloro-2-(methylamino)benzophenone, was selectively synthesized under our optimized conditions.
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.).
