I2-Mediated [3+2] annulation of methyl-azaarenes with alkyl 2-isocyanoacetates or amino acid ester hydrochlorides: selective synthesis of iodine-functionalized and non-iodine-functionalized fused imidazoles

被引：12

作者：

Hu, Yong-Ji ^{[1
]}

Zhou, Yu ^{[1
]}

Gao, Jing-Jing ^{[1
]}

Zhang, Han ^{[1
]}

Yang, Kai-Rui ^{[1
]}

Li, Jia-Jun ^{[1
]}

Yan, Xiao-Xin ^{[1
]}

Li, Yuan-Lin ^{[1
]}

Zhu, Yan-Ping ^{[1
]}

机构：

[1] Yantai Univ, Collaborat Innovat Ctr Adv Drug Delivery Syst & B, Key Lab Mol Pharmacol & Drug Evaluat, Sch Pharm,Minist Educ, Yantai 264005, Shandong, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2022年 / 9卷 / 05期

基金：

中国国家自然科学基金;

关键词：

NITROGEN-HETEROCYCLES; ISOCYANIDES; DERIVATIVES; CYCLIZATION; CYCLOADDITION; AMINATION; INSERTION; KETONES; ACCESS;

D O I：

10.1039/d1qo01940f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An I-2-mediated [3 + 2] annulation of methyl-azaarenes with alkyl 2-isocyanoacetates or amino acid ester hydrochlorides has been demonstrated. This strategy involves C equivalent to N bond cleavage of isocyanides and can selectively synthesize iodine-functionalized and non-iodine-functionalized fused imidazoles. Scaleup experiments and arylation, alkynylation, alkenylation and selenization of iodine-functionalized products demonstrated the potential applications of this reaction.

引用

页码：1403 / 1409

页数：7