Novel synthesis of 2-thiazolines

被引：45

作者：

Fernandez, X ^{[1
]}

Fellous, R ^{[1
]}

Duñach, E ^{[1
]}

机构：

[1] Univ Nice, Lab Aromes Synthese & Interact, F-06108 Nice 2, France

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 18期

关键词：

thiazolines; thiazolidines; oxidation; ruthenium-catalyzed; TBHP;

D O I：

10.1016/S0040-4039(00)00419-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of a series of 2-thiazolines was carried out under mild conditions from the corresponding thiazolidines, by a Ru-catalyzed/TBHP oxidation reaction conditions. The reaction was chemoselective towards the amine-imine oxidation and was also regioselective, affording the unsaturation at the 2-position of the heterocycle, even with thiazolidine substrates bearing ester groups at the 4-position. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：3381 / 3384

页数：4

共 25 条

[1] TOTAL SYNTHESIS OF THIANGAZOLE, A NOVEL INHIBITOR OF HIV-1 FROM POLYANGIUM SP [J].

BOYCE, RJ ;

MULQUEEN, GC ;

PATTENDEN, G .

TETRAHEDRON LETTERS, 1994, 35 (31) :5705-5708

[2]

BULTERY R, 1994, J AGR FOOD CHEM, V42, P791

[3] A one step synthesis of thiazolines from esters [J].

Busacca, CA ;

Dong, Y ;

Spinelli, EM .

TETRAHEDRON LETTERS, 1996, 37 (17) :2935-2938

[4] SYNTHESIS AND IN SOLUTION BEHAVIOR OF NEW 2-SUBSTITUTED-4-THIAZOLIDINECARBOXYLIC ACID-DERIVATIVES [J].

CHIARINO, D ;

FERRARIO, F ;

PELLACINI, F ;

SALA, A .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1989, 26 (03) :589-593

[5]

CORNEJO J, 1985, J ORG CHEM, V103, P5382

[6] FORMATION OF OXAZOLINES AND THIAZOLINES IN PEPTIDES BY THE MITSUNOBU REACTION [J].

GALEOTTI, N ;

MONTAGNE, C ;

PONCET, J ;

JOUIN, P .

TETRAHEDRON LETTERS, 1992, 33 (20) :2807-2810

[7] SYNTHESIS AND STRUCTURE OF 2-SUBSTITUTED DERIVATIVES OF 4-ETHYL(R) THIAZOLIDINE CARBOXYLATE [J].

HAMRI, A ;

PERA, MH ;

FILLION, H .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1987, 24 (06) :1629-1633

[8] NITROGEN-CONTAINING HETEROCYCLIC-COMPOUNDS IDENTIFIED IN THE VOLATILE FLAVOR CONSTITUENTS OF ROASTED BEEF [J].

HARTMAN, GJ ;

QI, ZJ ;

COLLINS, GJ ;

LEE, KN ;

HO, CT ;

CHANG, SS .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1983, 31 (05) :1030-1033

[9] Synthesis of curacin A, an antimitotic cyclopropane-thiazoline from the marine cyanobacterium Lyngbya majuscula [J].

Lai, JY ;

Yu, JR ;

Mekonnen, B ;

Falck, JR .

TETRAHEDRON LETTERS, 1996, 37 (40) :7167-7170

[10]

MACLEOD G, 1987, J FOOD SCI, V52, P42, DOI 10.1111/j.1365-2621.1987.tb13968.x

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