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

被引：10

作者：

Garduno-Alva, Azucena ^{[1
]}

Carmen Ortega-Alfaro, M. ^{[2
]}

Lopez-Cortes, Jose G. ^{[1
]}

Chavez, Isabel ^{[1
]}

Barroso-Flores, Joaquin ^{[3
]}

Toscano, Ruben A. ^{[1
]}

Rudler, Henri ^{[4
]}

Alvarez-Toledano, Cecilio ^{[1
]}

机构：

[1] Univ Nacl Autonoma Mexico, Inst Quim, Mexico City 04510, DF, Mexico

[2] Univ Nacl Autonoma Mexico, Inst Ciencias Nucl, Mexico City 04510, DF, Mexico

[3] UAEM UNAM, Ctr Conjunto Invest Quim Sustentable, Toluca 50200, Estado De Mexic, Mexico

[4] Univ Paris 06, Inst Parisien Chim Mol, CNRS, UMR 7201, F-75005 Paris 5, France

来源：

CANADIAN JOURNAL OF CHEMISTRY | 2012年 / 90卷 / 05期

关键词：

pyrazines; gamma-lactones; N-activation; UNSATURATED CARBOXYLIC-ACIDS; DOUBLE NUCLEOPHILIC-ADDITION; DELTA-LACTONES; 1,1-BIS(TRIMETHYLSILYLOXY)KETENE ACETALS; BIS(TRIMETHYLSILYL)KETENE ACETALS; ALLYLIC ACETATES; CYCLIZATION; ACCESS; ACTIVATION; PYRIDINES;

D O I：

10.1139/V2012-016

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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

引用

页码：469 / 482

页数：14

共 31 条

[1]

Ainsworth C., 1972, J ORGANOMET CHEM, V73, P34

[2] SIR92 - a program for automatic solution of crystal structures by direct methods [J].

ALTOMARE, A ;

CASCARANO, G ;

GIACOVAZZO, G ;

GUAGLIARDI, A ;

BURLA, MC ;

POLIDORI, G ;

CAMALLI, M .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1994, 27 :435-435

[3]

[Anonymous], 2001, SYNTH COMMUN, DOI DOI 10.1081/SCC-100105893

[4] Unexpected formation of 3,3a,4,7a-tetrahydrobenzofuran-2,5-diones as well as arene carboxylic acids upon formal double exo nucleophilic addition of R1R2C-COO- to anisolechromium tricarbonyl complexes [J].

Bellassoued, M ;

Chelain, E ;

Collot, J ;

Rudler, H ;

Vaissermann, J .

CHEMICAL COMMUNICATIONS, 1999, (02) :187-188

[5]

Comins D.L., 1996, ADV NITROGEN HETEROC, V2, P251

[6]

Frisch M. J., 2016, Gaussian 03 Revision B.03

[7] Synthesis of new polycyclic γ- and δ-lactones upon activation of, and nucleophilic additions to, diazines:: Influence of the activating agents [J].

Garduno-Alva, A. ;

Xu, Y. ;

Gualo-Soberanes, N. ;

Lopez-Cortes, J. ;

Rudler, H. ;

Parlier, A. ;

Ortega-Alfaro, M. C. ;

Alvarez-Toledano, C. ;

Toscano, R. A. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (21) :3714-3723

[8] Nitrogen-containing Heterocyclic quinones: A class of potential selective antitumor agents [J].

Garuti, Laura ;

Roberti, Marinella ;

Pizzirani, Daniela .

MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2007, 7 (05) :481-489

[9] An expedient approach to tetrahydrofuro[3,2-b]pyridine-2(3H)-ones via activation of pyridine N-oxide by triflic anhydride [J].

Gualo-Soberanes, N. ;

Ortega-Alfaro, M. C. ;

Lopez-Cortes, J. G. ;

Toscano, R. A. ;

Rudler, H. ;

Alvarez-Toledano, C. .

TETRAHEDRON LETTERS, 2010, 51 (24) :3186-3189

[10]

Katritzky A.R., 1984, Comprehensive Heterocyclic Chemistry, V3

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