THE INVENTION OF RADICAL REACTIONS .25. A CONVENIENT METHOD FOR THE SYNTHESIS OF THE ACYL DERIVATIVES OF N-HYDROXYPYRIDINE-2-THIONE

被引:70
作者
BARTON, DHR
SAMADI, M
机构
[1] Department of Chemistry, Texas A and M University, College Station
关键词
N-HYDROXYPYRIDINE-2-THIONE ACYL DERIVATIVES; TRIBUTYLPHOSPHINE; RADICAL CHEMISTRY;
D O I
10.1016/S0040-4020(01)88249-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of the readily available di-N-oxide- of 2-thiopyridine disulfide 6 with tributylphosphine in the presence of a carboxylic acid provides a convenient and high yielding synthesis of the acyl derivatives 2 of N-hydroxy-2-thio-pyridone. Application of this procedure to the acids 17 and 18 gave, after irradiation in the presence of t-butylthiol, the desired decarbaxylated derivatives in high (>90%) yield.
引用
收藏
页码:7083 / 7090
页数:8
相关论文
共 28 条
[1]   NON-PROTEINOGENIC AMINO-ACID SYNTHESIS - THE BETA-ANION DERIVED FROM ASPARTIC-ACID, AND ITS APPLICATION TO ALPHA-AMINO-ACID SYNTHESIS [J].
BALDWIN, JE ;
MOLONEY, MG ;
NORTH, M .
TETRAHEDRON, 1989, 45 (19) :6309-6318
[2]   NEW AND IMPROVED METHODS FOR THE RADICAL DECARBOXYLATION OF ACIDS [J].
BARTON, DHR ;
CRICH, D ;
MOTHERWELL, WB .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (17) :939-941
[3]   STEREOSPECIFICITY IN THE SYNTHESIS OF C-5 MODIFIED NUCLEOSIDES USING RADICAL CHEMISTRY - FURANOSIDIC CHAIN-LENGTHENING THROUGH C-4 [J].
BARTON, DHR ;
GERO, SD ;
QUICLETSIRE, B ;
SAMADI, M .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (20) :1372-1373
[4]   SYNTHESIS OF NOVEL ALPHA-AMINO-ACIDS AND DERIVATIVES USING RADICAL CHEMISTRY - SYNTHESIS OF L-ALPHA-AMINO-ADIPIC AND D-ALPHA-AMINO-ADIPIC ACIDS, L-ALPHA-AMINOPIMELIC ACID AND APPROPRIATE UNSATURATED DERIVATIVES [J].
BARTON, DHR ;
HERVE, Y ;
POTIER, P ;
THIERRY, J .
TETRAHEDRON, 1987, 43 (19) :4297-4308
[5]   SYNTHESIS OF 2S, 3AS, 7AS-PERHYDROINDOLE-2-CARBOXYLIC AND OF 2S, 3AR, 7AR-PERHYDROINDOLE-2-CARBOXYLIC ACID-DERIVATIVES FROM L-ASPARTIC ACID [J].
BARTON, DHR ;
GUILHEM, J ;
HERVE, Y ;
POTIER, P ;
THIERRY, J .
TETRAHEDRON LETTERS, 1987, 28 (13) :1413-1416
[6]   THE INVENTION OF NEW RADICAL CHAIN-REACTIONS .10. HIGH-YIELD RADICAL-ADDITION REACTIONS OF ALPHA-BETA-UNSATURATED NITROOLEFINS - AN EXPEDIENT CONSTRUCTION OF THE 25-HYDROXY-VITAMIN-D3 SIDE-CHAIN FROM BILE-ACIDS [J].
BARTON, DHR ;
TOGO, H ;
ZARD, SZ .
TETRAHEDRON, 1985, 41 (23) :5507-5516
[7]   REDUCTIVE RADICAL DECARBOXYLATION OF AMINO-ACIDS AND PEPTIDES [J].
BARTON, DHR ;
HERVE, Y ;
POTIER, P ;
THIERRY, J .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (19) :1298-1299
[8]   THE INVENTION OF RADICAL REACTIONS .18. A CONVENIENT SOLUTION TO THE 1-CARBON PROBLEM (R-CO2H-](R-CO2H)-C-13) [J].
BARTON, DHR ;
OZBALIK, N ;
VACHER, B .
TETRAHEDRON, 1988, 44 (12) :3501-3512
[9]   SYNTHESIS OF DISULFIDES VIA SULFENYLATION OF ALKYL AND ARYLDITHIOPYRIDINE N-OXIDES [J].
BARTON, DHR ;
CHEN, C ;
WALL, GM .
TETRAHEDRON, 1991, 47 (32) :6127-6138
[10]   THE FREE-RADICAL CHEMISTRY OF CARBOXYLIC ESTERS OF 2-SELENOPYRIDINE-N-OXIDE - A CONVENIENT SYNTHESIS OF (L)-VINYLGLYCINE [J].
BARTON, DHR ;
CRICH, D ;
HERVE, Y ;
POTIER, P ;
THIERRY, J .
TETRAHEDRON, 1985, 41 (19) :4347-4357