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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Research Article

Green Synthesis of Acylhydrazides Involving a Heterocyclic Moiety using Terminal Dihaloalkanes in Organic Salt Media under Solvent-Free Conditions

Author(s): Gholamhassan Imanzadeh*, Roghayyeh Asgharzadeh and Zahra Soltanzadeh

Volume 19, Issue 11, 2022

Published on: 25 March, 2022

Page: [1005 - 1012] Pages: 8

DOI: 10.2174/1570178619666220127123822

Price: $65

Abstract

This paper aimed at investigating the reaction of some acyl hydrazides with different terminal dibromoalkanes. This investigation revealed that acyl hydrazide by reacting with 1,4 and 1,5- dibromoalkanes in the presence of DABCO (1,4-diazabicyclo[2.2.2]octane) and TBAB (tetrabutylammonium bromide) underwent a facile intramolecular N2-double-alkylation to form pyrrolidine and piperidine ring derivatives under solvent-free conditions. Moreover, the alkylation of acyl hydrazide with 1,6-dibromohexane as a substrate produced the related N2-mono-alkylated derivatives under the same conditions. Interestingly, using K2CO3 as the base in this reaction for 1,6-dibromohexane led to acyl hydrazide containing an azepane ring. Surprisingly, direct alkylation of 4-nitrobenzohydrazide with 1,2-dibromoethane led to an oxadiazine ring derivative. The product yield was found to be 60- 85% in 6-12 h.

Keywords: Acyl hydrazide, dihaloalkane, heterocyclic compound, organic salt media, solvent-free conditions, medicinal chemistry.

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