The chemistry, synthetic routes and medicinal properties of vicinal diamines and imidazolines are discussed. Synthetic routes towards chemically and pharmaceutically important molecules containing vicinal diamine functionality are discussed in detail. This mini review article covers the new developments of diamine chemistry between 2000 and 2005.

This microreview presents the development of the catalytic aminohalogenation of olefins. The olefin substrates include electron‐deficient and functionalized ones, such as α,β‐unsaturated esters, α,β‐unsaturated ketones and α,β‐unsaturated nitriles. In addition, the first asymmetric aminohalogenation by the use of Evans chiral auxiliaries is also discussed. The convincing evidence is provided to support the aziridinium mechanism of aminohalogenation reaction. The applications of this reaction are described by converting vicinal haloamines into other important synthetic building blocks. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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The (13)C NMR shifts of 48 diazaphenanthrene-type alkaloids have been calculated at the B3LYP/6-311+G(2d,p) level of theory. The results support the structural reassignment of samoquasine A as 2.

[reaction: see text] The aminochlorination of methylenecyclopropanes (MCPs) 1 and vinylidenecyclopropanes (VCPs) has been explored with use of FeCl(3) (20 mol %) as a Lewis acid catalyst in acetonitrile under convenient mild conditions. The stereochemistry has been unambiguously confirmed by X-ray structural analysis. The aziridinium-based mechanism, accounting for both regio- and stereoselectivity, has been carefully studied. A linear free-energy relationship study of this reaction confirms consistency with the Hammet equation.

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A new direct electrophilic diamination reaction of alpha,beta-unsaturated ketones and esters has been established without the use of any metal catalysts. Three types of nitriles (CH(3)CN, CH(3)CH(2)CN, and CH(3)CH(2)CH(2)CN) were employed as nucleophilic nitrogen sources. A new mechanism has also been proposed to explain the resulting regio- and stereoselectivity.