Construction of Trisubstituted Hydrazones via Base-Mediated Cascade Condensation N-Alkylation

Wentao Hao; Shuo Gao; Hongyi Cui; Ding Ding; Shaohua Jiang; Chunyan Zhang; Yuqi Ji; Guoying Zhang

doi:10.1021/acs.joc.3c02621

Construction of Trisubstituted Hydrazones via Base-Mediated Cascade Condensation N-Alkylation

J Org Chem. 2024 Feb 16;89(4):2605-2621. doi: 10.1021/acs.joc.3c02621. Epub 2024 Feb 5.

Authors

Wentao Hao^{1

2

3}, Shuo Gao^{1

3}, Hongyi Cui^{1

3}, Ding Ding¹, Shaohua Jiang⁴, Chunyan Zhang², Yuqi Ji¹, Guoying Zhang¹

Affiliations

¹ State Key Laboratory of Coal Conversion, Institute of Coal Chemistry, Chinese Academy of Sciences, Taiyuan 030001, China.
² College of Ecology, Taiyuan University of Technology, Taiyuan 030001, China.
³ University of Chinese Academy of Sciences, Beijing 100049, China.
⁴ Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, International Innovation Center for Forest Chemicals and Materials, College of Materials Science and Engineering, Nanjing Forestry University, Nanjing 210037, China.

PMID: 38315164
DOI: 10.1021/acs.joc.3c02621

Abstract

A practical base-promoted tandem condensation N-alkylation reaction for the formation of trisubstituted hydrazones has been developed employing aldehydes and hydrazines with alkyl halides. Crucially, this reaction successfully overcomes chemoselectivity problems, allowing for the reaction of multiple components in a one-pot manner. Halo- and heterofunctional groups, as well as free hydroxyl and amino groups, are tolerated in this transformation to produce a wide range of trisubstituted hydrazones in good to excellent yields.