[3+3] Annulation via Ring Opening/Cyclization of Donor-Acceptor Cyclopropanes with (Un)symmetrical Ureas: A Quick Access to Highly Functionalized Tetrahydropyrimidinones

被引：23

作者：

Taily, Irshad Maajid ^{[1
]}

Saha, Debarshi ^{[1
]}

Banerjee, Prabal ^{[1
]}

机构：

[1] Indian Inst Technol Ropar, Dept Chem, Nangal Rd, Rupnagar 140001, Punjab, India

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 2019卷 / 48期

关键词：

Donor-acceptor cyclopropane; Unsymmetrical urea; Malonate; Tetrahydropyrimidinone; LEWIS-ACID; CYCLOADDITION; DERIVATIVES; 1,4-DIAMINATION; REACTIVITY; AZETIDINES; INHIBITORS; DISCOVERY; DIENES;

D O I：

10.1002/ejoc.201901400

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild and straight-forward access to pharmacologically privileged tetrahydropyrimidinones exploiting readily available Donor-Acceptor cyclopropanes (DACs) is reported. This methodology involves the Lewis acid catalyzed synthesis of uriedo-malonates from (un)symmetrical ureas and DACs followed by I-2-base mediated cyclization to their corresponding tetrahydropyrimidinones. The cyclization protocol involves nucleophilic attack of the nitrogen of urea on the newly generated electrophilic acceptor end of DAC. The post functionalization offered potential biologically active molecules.

引用

页码：7804 / 7813

页数：10

共 41 条

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[3] Tetrahydroquinolines via Stereospecific [3+3]-Annulation of Donor-Acceptor Cyclopropanes with Nitrosoarenes
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[4] Annulation via Ring Opening/Cyclization of Donor-Acceptor Cyclobutanes with 2-Naphthols: Access to Highly Functionalized Naphthalene-Fused Oxepines
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[8] Triazene-Activated Donor-Acceptor Cyclopropanes: Ring-Opening and (3+2) Annulation Reactions
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