Three-component reaction between triphenylphosphine, dialkyl acetylenedicarboxylate and 4-amino-5-alkyl-2,4-dihydro-1,2,4-triazole-3-thiones: an efficient one-pot synthesis of stable phosphorus ylides

Abstract

Protonation of the reactive 1:1 intermediate produced in the reaction between dialkyl acetylenedicarboxylates and triphenylphosphine by 4-amino-5-alkyl-2,4-dihydro-1,2,4-triazole-3-thione leads to vinylphosphonium salts which undergo Michael addition with the conjugate base of the NH-acid to produce highly functionalized, salt-free phosphorus ylides in excellent yields.

Keywords:

• addition reaction
• dialkyl acetylenedicarboxylates
• phosphorus ylides
• triphenylphosphine
• NH-acid

Acknowledgements

We gratefully acknowledge the financial support from the Research Council of Islamic Azad University of Yazd and The Islamic Azad University of Zahedan of Iran.