6476-32-0Relevant academic research and scientific papers
Decarbonylative Synthesis of Aryl Nitriles from Aromatic Esters and Organocyanides by a Nickel Catalyst
Iizumi, Keiichiro,Kurosawa, Miki B.,Isshiki, Ryota,Muto, Kei,Yamaguchi, Junichiro
supporting information, p. 1555 - 1559 (2020/11/10)
A decarbonylative cyanation of aromatic esters with aminoacetonitriles in the presence of a nickel catalyst was developed. The key to this reaction was the use of a thiophene-based diphosphine ligand, dcypt, permitting the synthesis of aryl nitrile without the generation of stoichiometric metal- or halogen-containing chemical wastes. A wide range of aromatic esters, including hetarenes and pharmaceutical molecules, can be converted into aryl nitriles.
Three-Component Synthesis of Dibenzoxazepinamines and Dibenzothiazepinamines under Transition-Metal-Free Conditions
Chen, Shanping,Deng, Guo-Jun,Fang, Fang,Jiang, Shuxin,Lei, Hanwen
, p. 15658 - 15664 (2021/11/12)
A convenient and efficient strategy for the synthesis of dibenzoxazepinamines and dibenzothiazepinamines has been developed. This three-component approach started from 2-nitrobenzaldehydes, 2-aminophenols, and methoxyammonium chlorides under metal-free conditions. The protocol has the advantages of readily available starting materials, simple and facile conditions, gram-scale synthesis, and broad substrate scope, providing an efficient and practical strategy for the preparation of potential drug-active dibenzoxazepinamines and dibenzothiazepinamines in one pot.
2,4-Diaminotriazines as anti-infective agents
De, Suparna S.,Vogalu, Siva K.,Ansari, Nazima,Patil, Rajendra,Sriram, Dharmarajan,Degani, Mariam S.
, p. 1211 - 1215 (2020/12/04)
Triazines are scaffolds of interest to medicinal chemists as they have a wide variety of pharmacological activities. Molecules with the triazine moiety have been explored extensively for their anti-infective potential. In this paper, we report a series of
Electrochemical Reductive Smiles Rearrangement for C-N Bond Formation
Chang, Xihao,Zhang, Qinglin,Guo, Chang
supporting information, p. 10 - 13 (2019/01/04)
A conceptually new and synthetically valuable radical Smiles rearrangement reaction is reported under undivided electrolytic conditions. This protocol employs an entirely new strategy for the electrochemical radical Smiles rearrangement. Remarkably, an amidyl radical generated from the cleavage of the N-O bond under reductive electrolytic conditions plays a crucial role in this transformation. Various hydroxylamine derivatives bearing different substituents are suitable in this electrochemical transformation, furnishing the corresponding amides in up to 86% yield.
PYRAZOLO-TRIAZINE AND/OR PYRAZOLO-PYRIMIDINE DERIVATIVES AS SELECTIVE INHIBITOR OF CYCLIN DEPENDENT KINASE
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Page/Page column 50; 60, (2019/11/04)
The present invention relates to pyrazolo[1,5-a][1,3,5]triazine and pyrazolo[l,5-a]pyrimidine derivatives and/or pharmaceutically acceptable salts thereof, the use of these derivatives as pharmaceutically active agents, especially for the prophylaxis and/or treatment of cell proliferative diseases, inflammatory diseases, immunological diseases, cardiovascular diseases and infectious diseases. Furthermore, the present invention is directed towards pharmaceutical compositions containing at least one of the pyrazolo[1,5-a][1,3,5]triazine and pyrazolo[1,5-a]pyrimidine derivatives and/or pharmaceutically acceptable salts thereof.
Formal Aniline Synthesis from Phenols through Deoxygenative N-Centered Radical Substitution
Lardy, Samuel W.,Luong, Kristine C.,Schmidt, Valerie A.
supporting information, p. 15267 - 15271 (2019/12/11)
Phenolic, lignin-derived substrates have emerged as desirable biorenewable chemical feedstocks for coupling reactions. A radical-mediated conversion of phenol derivatives to anilines is reported, using unfunctionalized hydroxamic acids as the N-centered radical source. The applicability of this triethyl phosphite mediated O-atom transfer approach, which tolerates a range of steric and electronic demands to naturally occurring phenols and lignin models, has been demonstrated in this work to access the corresponding aniline derivatives.
Transformation of aromatic bromides into aromatic nitriles with n-BuLi, pivalonitrile, and iodine under metal cyanide-free conditions
Uchida, Ko,Togo, Hideo
, (2019/09/04)
Various aromatic nitriles could be obtained in good yields by the treatment of aryl bromides with n-butyllithium and then pivalonitrile, followed by the treatment with molecular iodine at 70 °C, without metal cyanides under transition-metal-free conditions. The present reaction proceeds through the radical β-elimination of imino-nitrogen-centered radicals formed from the reactions of imines and N-iodoimines under warming conditions.
Efficient Aryl Migration from an Aryl Ether to a Carboxylic Acid Group To Form an Ester by Visible-Light Photoredox Catalysis
Wang, Shao-Feng,Cao, Xiao-Ping,Li, Yang
supporting information, p. 13809 - 13813 (2017/10/24)
We have developed a highly efficient aryl migration from an aryl ether to a carboxylic acid group through retro-Smiles rearrangement by visible-light photoredox catalysis at ambient temperature. Transition metals and a stoichiometric oxidant and base are avoided in the transformation. Inspired by the high efficiency of this transformation and the fundamental importance of C?O bond cleavage, we developed a novel approach to the C?O cleavage of a biaryl ether to form two phenolic compounds, as demonstrated by a one-pot, two-step gram-scale reaction under mild conditions. The aryl migration exhibits broad scope and can be applied to the synthesis of pharmaceutical compounds, such as guacetisal. Primary mechanistic studies indicate that the catalytic cycle occurs by a reductive quenching pathway.
Direct C-H Cyanation of Arenes via Organic Photoredox Catalysis
McManus, Joshua B.,Nicewicz, David A.
supporting information, p. 2880 - 2883 (2017/03/11)
Methods for the direct C-H functionalization of aromatic compounds are in demand for a variety of applications, including the synthesis of agrochemicals, pharmaceuticals, and materials. Herein, we disclose the construction of aromatic nitriles via direct C-H functionalization using an acridinium photoredox catalyst and trimethylsilyl cyanide under an aerobic atmosphere. The reaction proceeds at room temperature under mild conditions and has proven to be compatible with a variety of electron-donating and -withdrawing groups, halogens, and nitrogen- and oxygen-containing heterocycles, as well as aromatic-containing pharmaceutical agents.
Base-promoted synthesis of dibenzoxazepinamines and quinazolinimines under metal-free conditions
Feng, Jian-Bo,Wu, Xiao-Feng
, p. 4522 - 4526 (2015/09/15)
An interesting base-promoted protocol for the synthesis of dibenzo[b,f][1,4]oxazepin-11-amines and quinazolinimines has been developed. Started from commercially available 2-fluorobenzonitriles, 2-aminophenols and 2-aminoethanol, good to excellent yields
