Synthesis of Dialkyl 2–(4–oxopyridin–1(4H)–yl)dicarboxylates Through the Reaction of 4–hydroxypyridine and Dialkyl Acetylenedicarboxylate in the Presence of Triphenylphosphine

Bita Mohtat,¹* Zohre Najafi Azar,¹ Semiramis Nahavandian,¹ Hoorieh Djahaniani,² and Abbas Ahmadi¹

¹ Department of Chemistry, Karaj Branch, Islamic Azad University, Karaj, Iran. *b.mohtat@jooyan.org

² Department of Chemistry, East Tehran Branch, Islamic Azad University, Qiamdasht, Tehran, Iran.

Received March 16, 2011. ]]> Accepted June 2, 2011.

Abstract

4–Hydroxypyridine undergoes a smooth reaction with dialkyl acetylenedicarboxylates in the presence of triphenylphosphine (15 mol %) to produce the E/Z isomers of dialkyl 2–(4–oxopyridin–1(4H)–yl)but–2–enedioates in high yields.

Keywords: 4–Hydroxypyridine, dialkyl acetylenedicarboxylates, triphenylphosphine, dialkyl 2–(4–oxopyridin–1(4H)–yl)but–2–enedioates.

Resumen

4–Hidroxipiridina reacciona bajo condiciones suaves con acetilencarboxilatos de dialquilo en presencia de trietilfosfina (15% molar) para producer los isómeros E/Z de los 2–(4–oxopiridin–1(4H)–il)but–2–endioatos de dialquilo en rendimientos elevados.

Palabras clave: 4–Hidroxipiridina, acetilendicarboxilatos de dialquilo, trifenilfosfina, 2–(4–oxopiridin–1(4H)–il)but–2–endioatos de dialquilo.

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