ChemInform Abstract: A New Synthesis of Aromatic and Heteroaromatic Nitrogen Mustards via 3-Pyrrolines.

ChemInform Abstract

Pure 3-pyrroline (II) is obtained by cyclization of cis-1,4-dichloro-2-butene (I) with ammonia. Reaction of (II) with the nitro(het)aryl halides (III) yields the N-aryl-3-pyrrolines (IVa), (IVc), and (IVe) - (IVi). The compounds (IVb) and (IVd) cannot be prepared by this method. The derivatives (IV) are oxidatively cleaved with osmium tetroxide and sodium periodate. The crude dialdehydes are directly reduced with borane to give the bis(2-hydroxyethyl)amines (V) which can be converted to the nitrogen mustards (VI) by known methods.