Synthesis of Fused-Pyrazines via Palladium-Catalyzed Double Benzyl Isocyanide Insertion and Cross-Dehydrogenative Coupling

被引：24

作者：

Senadi, Gopal Chandru ^{[1
]}

Guo, Bing-Chun ^{[1
]}

Chang, Yu-Ching ^{[1
]}

Hu, Wan-Ping ^{[2
]}

Wang, Jeh-Jeng ^{[1
,3
]}

机构：

[1] Kaohsiung Med Univ, Dept Med & Appl Chem, 100 Shiquan 1st Rd, Kaohsiung 807, Taiwan

[2] Kaohsiung Med Univ, Dept Biotechnol, 100 Shiquan 1st Rd, Kaohsiung 807, Taiwan

[3] Kaohsiung Med Univ Hosp, Dept Med Res, 100 Tzyou 1st Rd, Kaohsiung 807, Taiwan

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2018年 / 360卷 / 03期

关键词：

benzyl isocyanide; catalysis; cross-dehydrogenative coupling (CDC); fused pyrazines; palladium; KINASE INHIBITORS; PYRROLOPYRAZINES; OXIMES; CYCLIZATION; ALOISINES; DERIVATIVES; MECHANISM; POTENT; ROUTE;

D O I：

10.1002/adsc.201701202

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A palladium-catalyzed cascade reaction has been realized for the synthesis of 5H-pyrrolo[2,3-b] pyrazines and 5H-pyrazino[2,3-b]indoles from benzyl isocyanide by choosing o-pivaloyloximes or o-iodoanilines as a suitable substrate. The key steps involved are (i) oxidative addition of palladium through N-O or C-I cleavage; (ii) migratory double isocyanide insertion; and (iii) cross-dehydrogenative coupling. Notable features are good functional group tolerance as well as formation of three C-C and one C-N bonds.

引用

页码：491 / 501

页数：11

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