One-Pot Synthesis of Triazolobenzodiazepines Through Decarboxylative [3 + 2] Cycloaddition of Nonstabilized Azomethine Ylides and Cu-Free Click Reactions

Xiaoming Ma; Xiaofeng Zhang; Weiqi Qiu; Wensheng Zhang; Bruce Wan; Jason Evans; Wei Zhang

doi:10.3390/molecules24030601

One-Pot Synthesis of Triazolobenzodiazepines Through Decarboxylative [3 + 2] Cycloaddition of Nonstabilized Azomethine Ylides and Cu-Free Click Reactions

Molecules. 2019 Feb 8;24(3):601. doi: 10.3390/molecules24030601.

Authors

Xiaoming Ma¹, Xiaofeng Zhang², Weiqi Qiu³, Wensheng Zhang⁴, Bruce Wan⁵, Jason Evans⁶, Wei Zhang⁷

Affiliations

¹ School of Pharmaceutical Engineering and Life Science, Changzhou University, Changzhou 213164, China. mxm.wuxi@cczu.edu.cn.
² Department of Chemistry, University of Massachusetts Boston, 100 Morrissey Boulevard, Boston, MA 02125, USA. xfxiaofengzhang@gmail.com.
³ Department of Chemistry, University of Massachusetts Boston, 100 Morrissey Boulevard, Boston, MA 02125, USA. Weiqi.Qiu001@umb.edu.
⁴ School of Science, Jiaozuo Teachers' College, 998 Shanyang Road, Jiaozuo 454100, China. tongjizws@163.com.
⁵ Department of Chemistry, University of Massachusetts Boston, 100 Morrissey Boulevard, Boston, MA 02125, USA. brucewan99@yahoo.com.
⁶ Department of Chemistry, University of Massachusetts Boston, 100 Morrissey Boulevard, Boston, MA 02125, USA. jason.evans@umb.edu.
⁷ Department of Chemistry, University of Massachusetts Boston, 100 Morrissey Boulevard, Boston, MA 02125, USA. wei2.zhang@umb.edu.

Abstract

A one-pot synthesis of triazolobenzodiazepine-containing polycyclic compounds is introduced. The reaction process involves a decarboxylative three-component [3 + 2] cycloaddition of nonstabilized azomethine ylides, N-propargylation, and intramolecular click reactions.

Keywords: click reaction; decarboxylative [3 + 2] cycloaddition; nonstabilized azomethine ylides; one-pot synthesis.

MeSH terms

Azepines / chemical synthesis
Azepines / chemistry*
Azo Compounds / chemistry*
Click Chemistry*
Copper / chemistry*
Cycloaddition Reaction*
Molecular Structure
Stereoisomerism
Thiosemicarbazones / chemistry*
Triazoles / chemistry*

Substances

Azepines
Azo Compounds
Thiosemicarbazones
Triazoles
azomethine
Copper