Employing TosMIC as a C1N1 \"Two-Atom Synthon\" in Imidazole Synthesis by Neighboring Group Assistance Strategy. - 成果

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Employing TosMIC as a C1N1 "Two-Atom Synthon" in Imidazole Synthesis by Neighboring Group Assistance Strategy.

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成果类型：

期刊论文

作者：

Geng, Xiao;Wang, Can;Huang, Chun;Bao, Yang;Zhao, Peng;...

通讯作者：

Feng, Ling-ling（冯玲玲）;Feng, An-Xin

作者机构：

[Feng, Ling-ling; Huang, Chun; Feng, AX; Wang, Can; Feng, An-Xin; Zhou, You; Geng, Xiao; Bao, Yang; Zhao, Peng] Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China.

[Feng, An-Xin] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China.

通讯机构：

[Feng, LL; Feng, AX] C

[Feng, An-Xin] L

Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China.

Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China.

语种：

英文

期刊：

Organic Letters

ISSN：

1523-7060

年：

2019

卷：

期：

页码：

140-144

DOI：

10.1021/acs.orglett.9b04060

基金类别：

National Natural Science Foundation of ChinaNational Natural Science Foundation of China [21971080, 21971079, 21602070, 21772051, 21877046]; Fundamental Research Funds for the Central UniversitiesFundamental Research Funds for the Central Universities [CCNU15ZX002, CCNU18QN011]; 111 ProjectMinistry of Education, China - 111 Project [B17019]

机构署名：

本校为第一且通讯机构

院系归属：

化学学院

摘要：

We report an I2/FeCl3-co-promoted formal [2 + 2+1] annulation of aryl methyl ketones, 2-aminobenzyl alcohols, and p-toluenesulfonylmethyl isocyanide (TosMIC) by neighboring group (-CH2OH) assistance. This is a novel example of using the Van Leusen reagent as a unique C1N1 "two-atom synthon" in the synthesis of imidazoles. Preliminary mechanism studies showed that TsCH2NH2 might be the key intermediate in this reaction. Furthermore, this reaction not only unlocks a novel strategy for imidazo...

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