Regiospecific reduction of 5-benzylidene-2,4-thiazolidinediones and 4-oxo-2-thiazolidinethiones using lithium borohydride in pyridine and tetrahydrofuran

被引:61
作者
Giles, RG [1 ]
Lewis, NJ [1 ]
Quick, JK [1 ]
Sasse, MJ [1 ]
Urquhart, MWJ [1 ]
Youssef, L [1 ]
机构
[1] SmithKline Beecham Pharmaceut, Tonbridge TN11 9AN, Kent, England
关键词
regiospecific; conjugate reduction; lithium borohydride; benzylthiazolidinediones;
D O I
10.1016/S0040-4020(00)00361-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The novel regiospecific and general reduction of 5-benzylidene-2,4-thiazolidinediones and 5-benzylidene-4-oxo-2-thiazolidinethiones to the corresponding 5-benzyl derivatives has been accomplished using lithium borohydride in pyridine and tetrahydrofuran. Sodium borohydride and lithium chloride can also be used under these conditions, which represents a cheaper alternative to lithium borohydride. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4531 / 4537
页数:7
相关论文
共 20 条
[1]   UBER PYRROLIZIDINCHEMIE .3. EIGENSCHAFTEN UND CHEMISCHES VERHALTEN DER 2,5-DIOXO-5H-PYRROLO-[2,1-A] ISOINDOLE [J].
ADANK, K ;
VISCONTINI, M ;
PFENNING, HA ;
STOLL, WG .
HELVETICA CHIMICA ACTA, 1963, 46 (03) :1030-&
[2]   CONVENIENT PROCEDURE FOR THE CONVERSION OF SODIUM-BOROHYDRIDE INTO LITHIUM BOROHYDRIDE IN SIMPLE ETHER SOLVENTS [J].
BROWN, HC ;
CHOI, YM ;
NARASIMHAN, S .
INORGANIC CHEMISTRY, 1981, 20 (12) :4454-4456
[3]   A STUDY OF SOLVENTS FOR SODIUM BOROHYDRIDE AND THE EFFECT OF SOLVENT AND THE METAL ION ON BOROHYDRIDE REDUCTIONS [J].
BROWN, HC ;
MEAD, EJ ;
RAO, BCS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (23) :6209-6213
[4]   FACILE BIOCATALYTIC REDUCTION OF THE CARBON-CARBON DOUBLE-BOND OF 5-BENZYLIDENETHIAZOLIDINE-2,4-DIONES - SYNTHESIS OF (+/-)-5-(4-(2-[METHYL(2-PYRIDYL)AMINO]ETHOXY)BENZYL)THIAZOLIDINE-2,4-DIONE (BRL-49653), ITS (R)-(+)-ENANTIOMER AND ANALOGS [J].
CANTELLO, BCC ;
EGGLESTON, DS ;
HAIGH, D ;
HALTIWANGER, RC ;
HEATH, CM ;
HINDLEY, RM ;
JENNINGS, KR ;
SIME, JT ;
WORONIECKI, SR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (22) :3319-3324
[5]   SUBSTITUTED DIHYDROBENZOPYRAN AND DIHYDROBENZOFURAN THIAZOLIDINE-2,4-DIONES AS HYPOGLYCEMIC AGENTS [J].
CLARK, DA ;
GOLDSTEIN, SW ;
VOLKMANN, RA ;
EGGLER, JF ;
HOLLAND, GF ;
HULIN, B ;
STEVENSON, RW ;
KREUTTER, DK ;
GIBBS, EM ;
KRUPP, MN ;
MERRIGAN, P ;
KELBAUGH, PL ;
ANDREWS, EG ;
TICKNER, DL ;
SULESKE, RT ;
LAMPHERE, CH ;
RAJECKAS, FJ ;
KAPPELER, WH ;
MCDERMOTT, RE ;
HUTSON, NJ ;
JOHNSON, MR .
JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (01) :319-325
[6]   SELECTIVITY IN REDUCTION OF 2-CYCLOHEXENONE WITH NBU4BH4 IN VARIOUS SOLVENTS AND WITH NABH4 UNDER PHASE-TRANSFER CONDITIONS [J].
DINCAN, E ;
LOUPY, A .
TETRAHEDRON, 1981, 37 (06) :1171-1179
[7]   BOROHYDRIDE REDUCTION OF DELTA-1,9 2-OCTALONE - CATION INFLUENCE AND AMINE ADDITION EFFECTS [J].
DINCAN, E ;
LOUPY, A ;
MAIA, A .
TETRAHEDRON LETTERS, 1981, 22 (10) :941-944
[8]   Synthesis of enantioenriched 4-thiazolidinone (-)-LY213829 by chemoselective benzylamide cleavage in the presence of a C-S bond [J].
Hansen, MM ;
Harkness, AR ;
Khau, VV ;
Martinelli, MJ ;
Deeter, JB .
TETRAHEDRON-ASYMMETRY, 1996, 7 (09) :2515-2518
[9]  
JACKSON WR, 1965, J CHEM SOC C, P5281
[10]   REDUCTION OF CONJUGATED DOUBLE BONDS WITH SODIUM BOROHYDRIDE [J].
KADIN, SB .
JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (02) :620-&