Stereoselective synthesis of spirocyclic derivatives of functionalized 2,3,4,7-tetrahydro-1 H-azepines

被引：1

作者：

Iusupov, Ildar R. ^{[1
]}

Kurkin, Alexander V. ^{[1
]}

机构：

[1] Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119991, Russia

来源：

MENDELEEV COMMUNICATIONS | 2024年 / 34卷 / 02期

基金：

俄罗斯基础研究基金会;

关键词：

spirocycle; azepane; azepine; 1,2,3-triazole; 7-azaspiro[4.6]undec-9-ene; 8-azaspiro[5.6]dodec-10-ene; metathesis reaction; stereoselective synthesis; click chemistry; BIOLOGICAL-ACTIVITIES; INHIBITORS; POTENT; SCAFFOLDS; DISCOVERY; DESIGN; RCM;

D O I：

10.1016/j.mencom.2024.02.016

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A simple and effective stereoselective synthesis of unique azaspirocyclic 2,3,4,7-tetrahydro-1 H -azepine derivatives, namely, 7-azaspiro[4.6]undec-9-ene and 8-azaspiro[5.6]dodec-10-ene, from simple commercially available reagents was accomplished. Their key 1,2 -epoxy derivatives as individual diastereomers were obtained in nine steps with 31-32% overall yields. The possibility of synthesizing a library of small spiroheterocyclic molecules was exemplified by the N -Boc-protected (1 RS ,2 SR ,6 RS )-1,2-epoxy-8-aza- spiro[5.6]dodec-10-ene scaffold through simple chemical modifications of its epoxide function.

引用

页码：209 / 211

页数：3

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