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Issue 62, 2019
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DABCO bond cleavage for the synthesis of piperazine derivatives

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Abstract

The applications of DABCO (1,4-diazabicyclo[2.2.2]octane) in the synthesis of piperazine derivatives including biologically active compounds via C–N bond cleavage are investigated in this review. Different reagents such as alkyl halides, aryl(heteroary) halides, carboxylic acids, diaryliodonium salts, tosyl halides, activated alkynes, benzynes etc. were applied for the preparation of the corresponding quaternary ammonium salts of DABCO, which are very good electrophiles for various nucleophiles such as phenols, thiophenols, thiols, alcohols, aliphatic and aromatic amines, sulfinates, phthalimide, indoles, NaN3, triazole and terazoles, NaCN, enols and enolates, halides, carboxylic acid salts etc. Besides preactivated DABCO salts, the in situ activation of DABCO in multicomponent reactions is also an efficient tactic in synthetic organic chemistry for the diversity oriented synthesis of drug-like piperazine derivatives.

Graphical abstract: DABCO bond cleavage for the synthesis of piperazine derivatives

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Article information


Submitted
27 Sep 2019
Accepted
30 Oct 2019
First published
08 Nov 2019

This article is Open Access

RSC Adv., 2019,9, 36386-36409
Article type
Review Article

DABCO bond cleavage for the synthesis of piperazine derivatives

A. Z. Halimehjani and E. Badali, RSC Adv., 2019, 9, 36386
DOI: 10.1039/C9RA07870C

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