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

Mahsa Golmohammadi; Nader Noroozi Pesyan; Ertan Şahin

doi:10.1055/s-0043-1774930

Synthesis, Table of Contents

Synthesis 2024; 56(17): 2742-2746
DOI: 10.1055/s-0043-1774930

paper

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

Mahsa Golmohammadi

^aDepartment of Organic Chemistry, Faculty of Chemistry, Urmia University, 57159 Urmia, Iran

,

Nader Noroozi Pesyan ∗

^aDepartment of Organic Chemistry, Faculty of Chemistry, Urmia University, 57159 Urmia, Iran

,

Ertan Şahin

^bDepartment of Chemistry, Faculty of Science, Atatürk University, Erzurum

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Abstract

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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

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