α-Csp3-H Methylenation of Diketones to Synthesize Methylene-Bridged Bis-1,3-Dicarbonyl Compounds and Polysubstituted Pyridines Using the DMSO/Selectfluor System

被引：25

作者：

Gao, Yejun ^{[1
]}

Zhou, Dongheng ^{[1
]}

Ma, Yongmin ^{[1
]}

机构：

[1] Zhejiang Chinese Med Univ, Sch Pharmaceut Sci, Hangzhou 310053, Zhejiang, Peoples R China

来源：

CHEMISTRYSELECT | 2018年 / 3卷 / 32期

关键词：

C-H functionalization; DMSO; pyridines; Selectfluor; CATALYZED ALPHA-METHYLENATION; ONE-CARBON SOURCE; C-N CLEAVAGE; DIMETHYL-SULFOXIDE; ORGANIC-SYNTHESIS; H BONDS; DMSO; KETONES; OXIDATION; ACCESS;

D O I：

10.1002/slct.201801996

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A direct alpha-Csp(3)-H methylenation of 1,3-diketones to afford methylene-bridged bis-1,3-dicarbonyl derivatives using dimethyl sulfoxide (DMSO) as a one-carbon source was achieved in moderate to high yields in the presence of Selectfluor. The 1,3-diketones can also be efficiently converted into Hantzsch-type pyridines via one-pot three-component annulation reaction in the presence of DMSO and ammonium salt. The procedure avoids the use of transition metal catalysts and the reaction is efficient and operationally convenient.

引用

页码：9374 / 9377

页数：4

共 12 条

[1] Synthesis of Methylene-Bridged Bis-1,3-dicarbonyl Compounds under Aerobic Condition
Guo, Shengmei
Gong, Jiuhan
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CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2015, 35 (06) : 1348 - 1352
[2] Synthesis of methylene-bridged α,β-unsaturated ketones: α-Csp3-H methylenation of aromatic ketones using Selectfluor as a mild oxidant
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[3] Gold/copper-catalyzed activation of the aci-form of nitromethane in the synthesis of methylene-bridged bis-1,3-dicarbonyl compounds
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[4] Iodine-Catalyzed C-N Cleavage of Tertiary Amines: Synthesis of Methylene-Bridged Bis-1,3-dicarbonyl Compounds
Lu, Lin
Guo, Shengmei
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[5] Aerobic Oxidation of a Tertiary Aliphatic Amine Under Visible-Light Photocatalysis: Facile Synthesis of Methylene-Bridged Bis-1,3-dicarbonyl Compounds
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CHEMISTRY-AN ASIAN JOURNAL, 2012, 7 (12) : 2764 - 2767
[6] Iron-Catalyzed Selective Oxidation of N-Methyl Amines: Highly Efficient Synthesis of Methylene-Bridged bis-1,3-Dicarbonyl Compounds
Li, Haijun
He, Zhiheng
Guo, Xingwei
Li, Wenjuan
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Li, Zhiping
ORGANIC LETTERS, 2009, 11 (18) : 4176 - 4179
[7] Metal-free synthesis of methylene-bridged bis-1,3-dicarbonyl compounds via oxidative C-C bond cleavage of tertiary aliphatic amines
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RSC ADVANCES, 2014, 4 (51): : 26783 - 26786
[8] Functionalization of aliphatic tertiary amines mediated by hexachloroethane/cat. copper: synthesis of propargylic amines and methylene-bridged bis-1,3-dicarbonyl derivatives
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[9] Visible-light photoredox-mediated oxidation of N-methyl tertiaryamines under catalyst free conditions: Direct synthesis of methylene-bridged bis-1,3-dicarbonyl compounds
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CHINESE CHEMICAL LETTERS, 2014, 25 (04) : 545 - 548
[10] Visible-light photoredox-mediated oxidation of N-methyl tertiaryamines under catalyst free conditions:Direct synthesis of methylene-bridged bis-1,3-dicarbonyl compounds
Xiao-Jun Dai
Xiao-Liang Xu
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ChineseChemicalLetters, 2014, 25 (04) : 545 - 548

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