Vinyltriphenylphosphonium Salt-Mediated Efficient Synthesis of Imino­phosphoranes Derived from 2-Aminothiazoles

Abstract

Crystalline phosphorus ylides are obtained in excellent yields from the 1:1:1 addition reaction between triphenylphosphine, dimethyl acetylenedicarboxylate and 2-aminothiazoles, such as 2-aminothiazole, 2-amino-3-methylthiazole, 2-aminothiazoline, 2-aminobenzothiazole, or 2-amino-7-methylbenzothiazole. These stabilized phosphoranes undergo a smooth intramolecular reaction in boiling toluene to produce the corresponding iminophosphoranes in excellent yields.

Key words

phosphorus imines - phosphorus ylides - 2-aminothiazoles - triphenylphosphine - alkynes

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