Electrophilic α-thiocyanation of chiral and achiral N-acyl imides.: A convenient route to 5-substituted and 5,5-disubstituted 2,4-thiazolidinediones

被引：68

作者：

Falck, J. R. ^{[1
]}

Gao, Shuanhu

Prasad, Ravi Naga

Koduru, Sreenivasulu Reddy

机构：

[1] Univ Texas SW Med Ctr Dallas, Dept Biochem, Dallas, TX 75390 USA

[2] Univ Texas SW Med Ctr Dallas, Dept Pharmacol, Dallas, TX 75390 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2008年 / 18卷 / 06期

关键词：

D O I：

10.1016/j.bmcl.2008.02.034

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Electrophilic alpha-thiocyanation of N-acyl carboximides using N-thiocyanatosuccinimide and hydrolytic cyclization of the adducts affords 5-substituted and 5,5-disubstituted 2,4-thiazolidinediones in good overall yields. alpha-Thiocyanation of chiral N-acyl carboximides proceeds with excellent diastereoselectivity, although partial racemization occurs during subsequent cyclization. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：1768 / 1771

页数：4

共 17 条

[1] Thiazolidinediones in dermatology [J].

Boyd, Alan S. .

INTERNATIONAL JOURNAL OF DERMATOLOGY, 2007, 46 (06) :557-563

[2] Dialkyl thiazolidiones [J].

Doran, WJ ;

Shonle, HA .

JOURNAL OF ORGANIC CHEMISTRY, 1938, 3 (03) :193-197

[3] Thiazolidinediones for the treatment of type 2 diabetes [J].

Elte, J. W. F. ;

Blickle, J. F. .

EUROPEAN JOURNAL OF INTERNAL MEDICINE, 2007, 18 (01) :18-25

[4] THE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS - ELECTROPHILIC AZIDATION OF CHIRAL IMIDE ENOLATES, A PRACTICAL APPROACH TO THE SYNTHESIS OF (R)-ALPHA-AZIDO AND (S)-ALPHA-AZIDO CARBOXYLIC-ACIDS [J].

EVANS, DA ;

BRITTON, TC ;

ELLMAN, JA ;

DOROW, RL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (10) :4011-4030

[5] Stereoselective follow-up reactions of (S)-2-sulfanyl nitriles [J].

Gaupp, S ;

Effenberger, F .

TETRAHEDRON-ASYMMETRY, 1999, 10 (09) :1777-1786

[6] A NEW HOMOGENEOUS PLATINUM-CONTAINING CATALYST FOR THE HYDROLYSIS OF NITRILES [J].

GHAFFAR, T ;

PARKINS, AW .

TETRAHEDRON LETTERS, 1995, 36 (47) :8657-8660

[7] New oxadiazolidinedione derivatives as potent and selective human β3 agonists [J].

Hu, BH ;

Malamas, M ;

Ellingboe, J ;

Largis, E ;

Han, S ;

Mulvey, R ;

Tillett, J .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (08) :981-984

[8] SYNTHESIS OF CHIRAL ADENOSINE RECEPTOR RECOGNITION UNITS VIA A SHARPLESS ASYMMETRIC EPOXIDATION PROCEDURE [J].

LENTZ, NL ;

PEET, NP .

TETRAHEDRON LETTERS, 1990, 31 (06) :811-814

[9] Thiazolidinediones: novel treatments for cognitive deficits in mood disorders? [J].

McIntyre, Roger S. ;

Soczynska, Joanna K. ;

Woldeyohannes, Hanna ;

Lewis, Gary F. ;

Leiter, Lawrence A. ;

MacQueen, Glenda M. ;

Miranda, Andrew ;

Fulgosi, Don ;

Konarski, Jakub Z. ;

Kennedy, Sidney H. .

EXPERT OPINION ON PHARMACOTHERAPY, 2007, 8 (11) :1615-1628

[10] Thiazolidin-5-ones: Synthesis and reactions [J].

Metwally, M. A. ;

Etman, H. A. ;

Keshk, E. M. ;

Fekry, A. .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2006, 181 (05) :1039-1058

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