Acid-catalyzed chemodivergent reactions of 2,2-dimethoxyacetaldehyde and anilines

被引：4

作者：

Guo, Luxia ^{[1
]}

Chen, Zihao ^{[1
]}

Zhu, Hongmei ^{[1
]}

Li, Minghao ^{[1
]}

Gu, Yanlong ^{[1
,2
,3
]}

机构：

[1] Huazhong Univ Sci & Technol, Hubei Key Lab Mat Chem & Serv Failure, Wuhan 430074, Peoples R China

[2] Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China

[3] Shihezi Univ, Key Lab Green Proc Chem Engn Xinjiang Bingtuan, Shihezi 832004, Peoples R China

来源：

CHINESE CHEMICAL LETTERS | 2021年 / 32卷 / 04期

基金：

中国国家自然科学基金;

关键词：

Condition-determined reaction; Chemodivergent reaction; 2,2-Dimethoxyacetaldehyde; C-C bond cleavage; Heyns rearrangement; C BOND-CLEAVAGE; ALDEHYDES; KETONES; REARRANGEMENT; ACCESS;

D O I：

10.1016/j.cclet.2020.10.033

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Chemodivergent reactions of 2,2-dimethoxyacetaldehyde and anilines were described, which were established on the basis of either a C-C bond cleavage or a rearrangement process of a reaction intermediate. These reactions proceeded in a condition-determined manner with good functional group tolerance. In the first model, 2,2-dimethoxyacetaldehyde reacted with aniline to form a new C-N bond, in the presence of O-2, via a C-C bond cleavage reaction. However, in the second model, by performing the reaction in the absence of O-2, Heyns rearrangement occurred and generated a new C-O bond to form methyl phenylglycinate. Such condition-determined reactions not only offered the new way for value-added conversion of biomass-derived platform molecule, 2, 2-dimethoxyacetaldehyde, but also provided efficient methods for the synthesis of N-arylformamides and methyl phenylglycinates. (C) 2020 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

引用

页码：1419 / 1422

页数：4

共 39 条

[21] Homo- and Heteroannulation of sp3 C-H Bonds in Acetophenones for Divergent Synthesis of Thienothiazoles [J].