Synthesis of new γ-lactones from preactivated monosubstituted pyrazines and TMS

Synthesis of new γ-lactones from preactivated monosubstituted pyrazines and TMS–ketene acetals

Published:2012-05 Issue:5 Volume:90 Page:469-482
ISSN:0008-4042
Container-title:Canadian Journal of Chemistry
language:en
Short-container-title:Can. J. Chem.

Author:

Garduño-Alva Azucena¹,Ortega-Alfaro M. Carmen²,López-Cortés José G.¹,Chávez Isabel¹,Barroso-Flores Joaquin³,Toscano Rubén A.¹,Rudler Henri⁴,Álvarez-Toledano Cecilio¹

Affiliation:

1. Instituto de Química-UNAM, Circuito Exterior, Ciudad Universitaria, Coyoacán C. P. 04510, México, D. F.

2. Instituto de Ciencias Nucleares-UNAM, Circuito Exterior, Ciudad Universitaria, Coyoacán C. P. 04510, México, D. F.

3. Centro Conjunto de Investigación en Química Sustentable UAEM-UNAM. Car. Toluca-Atlacomulco, Km 14.5 Unidad San Cayetano. Personal de la UNAM. Toluca 50200, Estado de México, México.

4. Institut Parisien de Chimie Moléculaire, UMR CNRS 7201, Université Pierre et Marie Curie, 4 place Jussieu, 75005 Paris CEDEX 5, France.

Abstract

The double addition of bis(trimethylsilyl) ketene acetals (1a–1b, R1 = CH3, –(CH2)5–) to 2-substituted pyrazines promoted by triflic anhydride leads to γ-lactones in a single step. A systematic study involving electron-withdrawing and electron-donating groups (R2 = CN, COOMe, PhCH=CH, Cl, Me, OMe) in the pyrazine ring reveals a strong dependence of electronic effects on the regiochemistry of nucleophilic addition.

Publisher

Canadian Science Publishing

Subject

Organic Chemistry,General Chemistry,Catalysis

Link

http://www.nrcresearchpress.com/doi/pdf/10.1139/v2012-016

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