Vicinal Diamino Functionalities as Privileged Structural Elements in Biologically Active Compounds and Exploitation of their Synthetic Chemistry

Abstract

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.

Simple and Efficient Synthesis of N-Nitroethylenediamine Derivatives

“…1 They also serve as selective ligands in organic synthesis 2 and as synthons for heterocyclic compounds. 3 Relatively little attention has been paid to N-nitroethylenediamine (1) and its derivatives ( Figure 1).…”

Diastereoselective imino-pinacol coupling of chiral imines promoted by Mg(0) and a Grignard reagent

“…The reactions of 2-naphthalenylimine and p-tert-butylphenylimine provided the corresponding diamines in good yield with high diastereoselectivity, despite bulky substrates (entries 1, 2). Imines having electron-donating functional groups, for example, p-methyl, p-methoxy, and p-N,N-dimethylamino groups, could also tolerate this coupling reaction and were converted into their corresponding diamines in moderate yields (entries [3][4][5]. The structures of all the major isomers were assumed to be (SRRS) from comparison of chemical shifts in 1 H NMR spectra with those of 3a.…”

“…1 Diastereoselective coupling of chiral imines is especially useful for synthesis of chiral 1,2-diamine derivatives; a valuable class of compounds used as ligands of chiral catalysts in asymmetric synthesis 2 and as medicinal products in pharmaceutical chemistry. 3 Although this diastereoselective coupling has been extensively examined in terms of the intramolecular reaction of chiral diimines 4 and the intermolecular reaction employing chiral imines 5 or chiral activators, 6 most studies use costly reducing agents, such as Sm and SmI2, or a large excess of metals and acids. Moreover, only a few studies have investigated the conversion of the products obtained from intermolecular reactions into free ethylenediamines by the removal of the chiral auxiliary.…”

Transition‐Metal‐Catalyzed Diamination of Olefins

“…[1] Despite their extensive utility, the development of new methods allowing efficient preparation of 1,2-diamines remains a stimulating challenge. [1,2] Among the methods usually employed to generate such scaffolds, the direct oxidative alkene diamination presents an attractive strategy.…”