Bis[1H-imidazol-4(5)-yl]alkanes and 1,2,9,10- and 1,2,11,12-Tetraaminoalkane Tetrahydrochlorides

Bernhard Miller; Janina Altman; Wolfgang Beck

doi:10.1055/s-1997-4464

Synthesis 1997; 1997(3): 347-350
DOI: 10.1055/s-1997-4464

paper

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Bis[1H-imidazol-4(5)-yl]alkanes and 1,2,9,10- and 1,2,11,12-Tetraaminoalkane Tetrahydrochlorides

Bernhard Miller, Janina Altman, Wolfgang Beck^*

^*Institut für Anorganische Chemie der Universität München, Meiserstr. 1, D-80333 München, Germany, Fax +49(89)5902214

Abstract

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Bis[1H-imidazol-4(5)-yl]alkanes (n = 4-8) have been prepared by modified Bredereck cyclization of α,ω-dibromomethylalkanediones in formamide at 180°C. They undergo ring-cleavage acylation with methyl chloroformate to a mixture of N-formylated bis(enedicarbamates). Subsequent removal of formyl groups, reduction with palladium on charcoal and hydrolysis afford α,β,ω-1,ω-tetraaminoalkane tetrahydrochlorides.

bis[imidazol-4(5)-yl]alkanes - ring cleavage acylation - 1,2,9,10-tetraaminodecane - 1,2,11,12-tetraaminododecane

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