Copper(I)-catalyzed benzylic C(sp3)-H geminal difunctionalization: Successive oxidative intramolecular amidation and hydroxylation

被引：6

作者：

Zhang, Zhiguo ^{[1
]}

Wang, Songnan ^{[1
]}

Hu, Chunfang ^{[1
]}

Ma, Nana ^{[1
]}

Zhang, Guisheng ^{[1
]}

Liu, Qingfeng ^{[1
]}

机构：

[1] Henan Normal Univ, Henan Key Lab Organ Funct Mol & Drug Innovat, Collaborat Innovat Ctr Henan Prov Green Mfg Fine, Minist Educ,Sch Chem & Chem Engn,Key Lab Green Ch, Xinxiang 453007, Henan, Peoples R China

来源：

TETRAHEDRON | 2018年 / 74卷 / 52期

关键词：

Copper-catalysis; Benzylic C(sp(3))-H difunctionalization; Amidation; Hydroxylation; Pyrrolo[3,4-b]quinoxalinone; C-H BOND; ALPHA-AMINO-ACIDS; METAL-FREE; FACILE SYNTHESIS; FUNCTIONALIZATION; AMINATION; PORPHYRINS; ARYLATION; QUINOXALINE; DERIVATIVES;

D O I：

10.1016/j.tet.2018.11.023

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A selective copper(I)-catalyzed benzylic C(sp(3))-H geminal difunctionalization reaction of a benzylic-type sp(3) carbon was developed. This novel strategy allowed simultaneous introduction of amide and hydroxyl group in a highly selective and efficient way via successive oxidative intramolecular amidation and hydroxylation. This method was also applied to the synthesis of 3-hydroxy-2,3-dihydro-1H-pyrrolo[3,4-b]quinoxalinones from readily available 3-methyl-N-substituted quinoxaline-2-carboxamides in moderate to good yields. The five-membered cyclic hemiaminal moiety of the pyrrolo[3,4-b]quinoxalinones can serve as an intermediates for subsequent transformations into other useful functional groups. (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：7472 / 7479

页数：8

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