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

被引：13

作者：

Gualo-Soberanes, N. ^{[1
]}

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

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

Toscano, R. A. ^{[1
]}

Rudler, H. ^{[3
]}

Alvarez-Toledano, C. ^{[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] Univ Paris 06, CNRS, Chim Organ Lab, UMR 7611, F-75252 Paris 5, France

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 24期

关键词：

N-activation; 1,2-Dihydropyridines; Lactones; Ring-closing/decarboxylation; POLYCYCLIC GAMMA-LACTONES; ONE-STEP CONVERSION; DIRECT ARYLATION; DELTA-LACTONES; 1,1-BIS(TRIMETHYLSILYLOXY)KETENE ACETALS; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC ALLYLATION; NUCLEOPHILIC-ADDITION; SYNTHETIC UTILITY; DERIVATIVES;

D O I：

10.1016/j.tetlet.2010.04.030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The double addition of bis(trimethylsilyl) ketene acetals [R-1, R-2 = CH3, -(CH2)(5)-] to pyridine N-oxide promoted by triflic anhydride under mild conditions generates N-[(trifluoromethane)sulfonyl-1,2-dihydropyridine-2,4-dicarboxylic acids 2a-b. Subsequent reaction of these acids upon iodolactonization conditions affords tetrahydrofuro[3,2-b]pyridine-2(3H)-ones 3a-b containing an exo-insaturation on the products as a result of an unexpected decarboxylation. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：3186 / 3189

页数：4

共 64 条

[1]

ALBINI A, 1993, SYNTHESIS-STUTTGART, P263

[2]

Albini A., 1991, HETEROCYCLIC N OXIDE

[3] Synthesis of 2-substituted pyridines via a regiospecific alkylation, alkynylation, and arylation of pyridine N-oxides [J].

Andersson, Hans ;

Almqvist, Fredrik ;

Olsson, Roger .

ORGANIC LETTERS, 2007, 9 (07) :1335-1337

[4] Reaction of pyridine N-oxides with Grignard reagents:: a stereodefined synthesis of substituted dienal oximes [J].

Andersson, Hans ;

Wang, Xiaoyang ;

Bjorklund, Mikael ;

Olsson, Roger ;

Almqvist, Fredrik .

TETRAHEDRON LETTERS, 2007, 48 (39) :6941-6944

[5] The Regio- and Stereoselective Synthesis of trans-2,3-Dihydropyridine N-oxides and Piperidines [J].

Andersson, Hans ;

Gustafsson, Magnits ;

Bostrom, Dan ;

Olsson, Roger ;

Almqvist, Fredrik .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (18) :3288-3291

[6] Pyridine N-oxide derivatives are inhibitory to the human SARS and feline infectious peritonitis coronavirus in cell culture [J].

Balzarini, J ;

Keyaerts, E ;

Vijgen, L ;

Vandermeer, F ;

Stevens, M ;

De Clercq, E ;

Egberink, H ;

Van Ranst, M .

JOURNAL OF ANTIMICROBIAL CHEMOTHERAPY, 2006, 57 (03) :472-481

[7] Pyridine N-oxide derivatives: unusual anti-HIV compounds with multiple mechanisms of antiviral action [J].

Balzarini, J ;

Stevens, M ;

De Clercq, E ;

Schols, D ;

Pannecouque, C .

JOURNAL OF ANTIMICROBIAL CHEMOTHERAPY, 2005, 55 (02) :135-138

[8] Chemical transformations induced by triflic anhydride [J].

Baraznenok, IL ;

Nenajdenko, VG ;

Balenkova, ES .

TETRAHEDRON, 2000, 56 (20) :3077-3119

[9] A solution to the 2-pyridyl organometallic cross-coupling problem:: Regioselective catalytic direct arylation of pyridine N-oxides [J].

Campeau, LC ;

Rousseaux, S ;

Fagnou, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (51) :18020-18021

[10] C2, C5, and C4 azole N-oxide direct arylation including room-temperature reactions [J].

Campeau, Louis-Charles ;

Bertrand-Laperle, Megan ;

Leclerc, Jean-Philippe ;

Villemure, Elisia ;

Gorelsky, Serge ;

Fagnou, Keith .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (11) :3276-+

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