380626-88-0Relevant articles and documents
Electrochemical oxidation synergizing with Br?nsted-acid catalysis leads to [4 + 2] annulation for the synthesis of pyrazines
Liu, Kun,Song, Chunlan,Wu, Jiarong,Deng, Yuqi,Tang, Shan,Lei, Aiwen
supporting information, p. 765 - 769 (2019/02/27)
An electrochemical dehydrogenative [4 + 2] annulation for the synthesis of pyrazines has been developed under undivided electrolytic conditions. In this protocol, neither external chemical oxidants nor transition-metal catalysts are needed, and a wide range of substituted pyrazines could be obtained from simple ketones and diamines in high efficiencies. Of note is that this electrolysis could also be extended for the construction of biheteroarenes and large π systems with good yields.
Synthesis of Chiral Piperazines via Hydrogenation of Pyrazines Activated by Alkyl Halides
Huang, Wen-Xue,Liu, Lian-Jin,Wu, Bo,Feng, Guang-Shou,Wang, Baomin,Zhou, Yong-Gui
supporting information, p. 3082 - 3085 (2016/07/13)
A facile method has been developed for the synthesis of chiral piperazines through Ir-catalyzed hydrogenation of pyrazines activated by alkyl halides, giving a wide range of chiral piperazines including 3-substituted as well as 2,3- and 3,5-disubstituted
Iron-catalyzed cross-coupling of electron-deficient heterocycles and quinone with organoboron species via innate C-H functionalization: Application in total synthesis of pyrazine alkaloid botryllazine A
Singh, Parvinder Pal,Aithagani, Sravan Kumar,Yadav, Mahipal,Singh, Varun Pratap,Vishwakarma, Ram A.
, p. 2639 - 2648 (2013/04/24)
Here, we report an iron-catalyzed cross-coupling reaction of electron-deficient heterocycles and quinone with organoboron species via innate C-H functionalization. Iron(II) acetylacetonate along with oxidant (K 2S2O8) and phase-transfer catalyst (TBAB) under open flask conditions efficiently catalyzed the cross-coupling of pyrazine with arylboronic acids and gave monoarylated products in good to excellent yields. Optimized conditions also worked for other heterocylces such as quinoxalines, pyridines, quinoline, and isoquinoline as well as quinones. In addition, we demonstrated as a first example its application for the synthesis of anticancer marine pyrazine alkaloid botryllazine A.