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Synthesis
DOI: 10.1055/s-0043-1774930
paper

An Efficient Promising Direction for the Synthesis of Dispirotripiperazine (6-6-6 DSTP) Core

Mahsa Golmohammadi
a   Department of Organic Chemistry, Faculty of Chemistry, Urmia University, 57159 Urmia, Iran
,
Nader Noroozi Pesyan  ∗
a   Department of Organic Chemistry, Faculty of Chemistry, Urmia University, 57159 Urmia, Iran
,
Ertan Şahin
b   Department of Chemistry, Faculty of Science, Atatürk University, Erzurum
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Abstract

A new and facile route for the one-pot synthesis of 3,12-dicyano-3,6,9,12-tetraazadispiro[5.2.59.26]hexadecane-6,9-diium dibromide as a dispirotripiperazine source was introduced by the simple reaction of 1,4-diazabicyclo[2.2.2]octane (DABCO) with cyanogen bromide (BrCN) under mild condition at room temperature. The hydrolysis of dicyanamide moieties in the prepared dispiro compound gave 3,12-diaza-6,9-diazoniadispiro[5.2.5.2]hexadecane dibromide with the dispirotripiperazine (6-6-6) core. The molecular structure of the new compound was characterized by FT-IR, 1H, 13C, HSQC NMR spectroscopy, mass and CHN analysis, and X-ray crystallography technique.

Key words

dispirotripiperazine - cyanogen bromide - DABCO - (6-6-6) DSTP - one pot

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0043-1774930.
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Publication History

Received: 27 November 2023

Accepted after revision: 06 June 2024

Article published online:
26 June 2024

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