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

Mehdi Adib; Manizheh Mostofi; Khadijeh Ghanbary; Hamid Reza Bijanzadeh

doi:10.1055/s-2005-865297

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

Mehdi Adib*^a, Manizheh Mostofi^a, Khadijeh Ghanbary^a, Hamid Reza Bijanzadeh^b
^a Department of Chemistry, Faculty of Science, University of Tehran, Tehran, Iran
Fax: +98(21)6495291; e-Mail: madib@khayam.ut.ac.ir;
^b Department of Chemistry, Tarbiat Modarres University, Tehran, Iran

Abstract

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

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