Competition between cyclisation and bisimine formation in the reaction of 1, 3-diaminopropanes with aromatic aldehydes

JM Locke, R Griffith, TD Bailey, RL Crumbie

Index: Locke, Julie M.; Griffith, Renate; Bailey, Trevor D.; Crumbie, Robyn L. Tetrahedron, 2009 , vol. 65, # 51 p. 10685 - 10692

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Citation Number: 12

Abstract

Condensation of 1, 3-diamines with aldehydes or ketones gives rise to two major products, the hexahydropyrimidine and the bisimine. Experimental studies of the reaction between a range of aromatic aldehydes and 1, 3-diaminopropane or 1, 3-diamino-2-propanol establish that the hexahydropyrimidine is favoured by the less nucleophilic amine and by the presence of electron withdrawing groups on the aryl ring of the aldehyde. Calculations ...