86731-84-2Relevant academic research and scientific papers
N, N, N', N'-Tetramethylethylenediamine-Enabled Photoredox-Catalyzed C-H Methylation of N-Heteroarenes
Liu, Fang,Ye, Zhi-Peng,Hu, Yuan-Zhuo,Gao, Jie,Zheng, Lan,Chen, Kai,Xiang, Hao-Yue,Chen, Xiao-Qing,Yang, Hua
, p. 11905 - 11914 (2021/08/24)
Aiming at the valuable methylation process, readily available and inexpensive N,N,N′,N′-tetramethylethylenediamine (TMEDA) was first identified as a new methyl source in photoredox-catalyzed transformation in this work. By virtue of this simple methylating reagent, a facile and practical protocol for the direct C-H methylation of N-heteroarenes was developed, featuring mild reaction conditions, broad substrate scope, and scalability. Mechanistic studies disclosed that a sequential photoredox, base-assisted proton shift, fragmentation, and tautomerization process was essentially involved.
C?H Methylation of Iminoamido Heterocycles with Sulfur Ylides**
Ghosh, Prithwish,Kwon, Na Yeon,Kim, Saegun,Han, Sangil,Lee, Suk Hun,An, Won,Mishra, Neeraj Kumar,Han, Soo Bong,Kim, In Su
supporting information, p. 191 - 196 (2020/10/29)
The direct methylation of N-heterocycles is an important transformation for the advancement of pharmaceuticals, agrochemicals, functional materials, and other chemical entities. Herein, the unprecedented C(sp2)-H methylation of iminoamido heterocycles as nucleoside base analogues is described. Notably, trimethylsulfoxonium salt was employed as a methylating agent under aqueous conditions. A wide substrate scope and excellent level of functional-group tolerance were attained. Moreover, this method can be readily applied to the site-selective methylation of azauracil nucleosides. The feasibility of gram-scale reactions and various transformations of the products highlight the synthetic potential of the developed method. Combined deuterium-labeling experiments aided the elucidation of a plausible reaction mechanism.
Synthesis of π-Extended Heterocycles via Rh(III)-Catalyzed Oxidative Annulation of 5-Aryl Pyrazinones with Alkynes
Oh, Harin,Byun, Hee Won,Moon, Kyeongwon,Kim, Saegun,Ghosh, Prithwish,An, Won,Kwak, Jong Hwan,Park, Jung Su,Mishra, Neeraj Kumar,Kim, In Su
, p. 16349 - 16360 (2021/10/20)
The Rh(III)-catalyzed C-H functionalization and subsequent oxidative annulation between 5-aryl pyrazinones and internal alkynes are reported. This protocol provides facile access to a wide range of pyrazinone-linked naphthalenes via the C(sp2)-H alkenylat
FORMULATIONS CONTAINING PYRIDAZINE COMPOUNDS
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Page/Page column 40-41, (2010/01/31)
The invention relates to chemical compounds, compositions and methods of making and using the same. In particular, the invention provides selected pyridazine compounds of the formula I are independently hydrogen, hydroxyl, alkyl, alkenyl, alkynyl, alkylene, alkenylene, alkoxy, alkenyloxy, cycloalkyl, cycloalkenyl, cycloalkynyl, cycloalkoxy, aryl, aryloxy, arylalkoxy, aroyl, heteroaryl, heterocyclic, acyl, acyloxy, amino, imino, azido, thiol, thioalkyl, thioalkoxy, thioaryl, nitro, cyano, halo, sulfate, sulfenyl, sulfinyl, sulfonyl, sulfonate, sulfoxide, silyl, silyloxy, silylalkyl, silylthio, ═O, ═S, phosphonate, ureido, carboxyl, carbonyl, carbamoyl, or carboxamide; and X is optionally substituted pyrimidinyl or pyridazinyl, an isomer, a pharmaceutically acceptable salt, or derivative thereof. The invention additional relates to compositions comprising the compounds, and methods of using the compounds and compositions for modulation of cellular pathways, for treatment or prevention of inflammatory diseases, for research, drug screening, and therapeutic applications.
Concise synthesis of 1H-pyrazin-2-ones and 2-aminopyrazines
Adam, Isabelle,Orain, David,Meier, Peter
, p. 2031 - 2033 (2007/10/03)
Convenient syntheses of 1H-pyrazin-2-ones and 2-aminopyrazines are described. By coupling Boc-protected amino acids with α-amino ketones or with amino alcohols and subsequent oxidation, 1H-pyrazin-2-ones were obtained. Transformation into the corresponding pyrazine triflates and substitution with primary or secondary amines led to 2-aminopyrazines. Since these syntheses take advantage of the use of readily available starting materials (e.g., amino acids, aminoalcohols and amines) a variety of the entitled structures can be obtained in few, high yielding steps.
Studies on pyrazines. Part 34. Synthetic approach, stability and tautomerism of 2,6-dihydroxypyrazines
Sato, Nobuhiro,Matsumoto, Kaori,Takishima, Masayuki,Mochizuki, Katsura
, p. 3167 - 3172 (2007/10/03)
Demethylation of 2,6-dimethoxy-3,5-diphenylpyrazine with iodotrimethylsilane gives the corresponding 2,6-dihydroxy- and 2-hydroxy-6-methoxy-pyrazines, whilst the 3-methyl-5-phenyl analogue affords only monohydroxy compounds. In contrast, 2,6-dimethoxy-3,5-dimethylpyrazine decomposes completely under the demethylation conditions. Hydrolysis of 2,6-diacetoxypyrazines succeeds only in the formation of 2,6-dihydroxy-3,5-diphenylpyrazine. The stability of 2,6-dihydroxypyrazines is discussed on the basis of observations made in the synthetic approach. In addition, it has been established, on the basis of UV spectral analysis, that the 2-hydroxy-6-methoxypyrazines obtained in our work exist predominantly in the hydroxypyrazine form rather than as 1,2-dihydropyrazin-2-ones.
Reactions of the Monoxides of 2,6-Disubstituted Pyrazines with Phosphoryl Chloride and Acetic Anhydride
Ohta, Akihiro,Imazeki, Akiko,Itoigawa, Yohko,Yamada, Hiroko,Suga, Chieko,et al.
, p. 311 - 320 (2007/10/02)
The monoxides of 2,6-dimethyl- (1), 2,6-diphenyl- (2), and 2-methyl-6-phenylpyrazines (3) were subjected to the reactions with phosphoryl chloride and acetic anhydride.Some reactions of the chloropyrazines and hydroxypyrazines obtained thus were also inve
