A New synthesis of highly fufictionalized 5-azaqumarines
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A New synthesis of highly fufictionalized 5-azaqumarines. Bita Mohtat a,Issa Ya\-ari,a,bHasan Zare b. Department of Chemistry, Islamic Azad [; niversity, Karadj, Iran aand Department of. Chemistry, Tarbiat Modarres University, Tehran, Iran a,b. Summary. 3-hydroxy. pyridine. undergoes a.

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A New synthesis of highly fufictionalized 5-azaqumarines

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A new synthesis of highly fufictionalized 5 azaqumarines

A New synthesis of highly fufictionalized 5-azaqumarines

Bita Mohtat a,Issa Ya\-ari,a,bHasan Zare b

.

Department of Chemistry, Islamic Azad [; niversity, Karadj, Iran aand Department of

Chemistry, Tarbiat Modarres University, Tehran, Iran a,b

Summary

3-hydroxy

pyridine

undergoes a

smooth

reaction

with

dialkyl

acetylenedicarboxylates in the presence of triphenylphosphine to produce phosphorus

ylide intermediates, which produce alkyl 2-oxo-2H-pyrano[3,2-b ]pyridine-4-carboxylate

3a-3d, and alkyl 6-«E)-1 ,2-di(alkoxycarbon~-I)vinyl)-2-oxo-2H-pyrano[3,2-b ]pyridine-4-

carboxylate 4a-4d. Under the same reaction conditions, di-tert-butyl or di-iso-propyl

acetylenedicarboxylate produces dialkyl 2-(5-hydroxypyridin-2-yl)but-2-enedioate

Sa-

Sb.

Key-vords: 3-hydroxypyridine; triphenylphosphine; acetylenic ester; phosphorus ylide.

Corresponding authors. Fax: +98(21)800654-1r;

E-mail: [email protected]

Introduction

The addition reaction between electron-deficient acetylenic compounds and nitrogen-

containing hetrocycles has been extensivel~' investigated [1-4]. We report herein that

dialkyl acetylenedicarboxylate undergoes addition reaction with 3-hydroxy pyridine in

the presence of triphenylphosphine, yielding alkyl 2-oxo-2H-pyrano[3,2-b ]pyridine-4-

carboxylate 3a-3d, and alkyl 6-«E)-1,2-di(alkoxycarbonyl)vinyl)-2-oxo-2H-pyrano[3,2-

b]pyridine-4-carboxylate 4a-4d. Under the same reaction conditions, di-tert-butyl or di-


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