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

来源：

TETRAHEDRON | 1992年 / 48卷 / 35期

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

页码：7083 / 7090

页数：8

共 28 条

[1] NON-PROTEINOGENIC AMINO-ACID SYNTHESIS - THE BETA-ANION DERIVED FROM ASPARTIC-ACID, AND ITS APPLICATION TO ALPHA-AMINO-ACID SYNTHESIS
BALDWIN, JE
MOLONEY, MG
NORTH, M
[J]. TETRAHEDRON, 1989, 45 (19) : 6309 - 6318
[2] NEW AND IMPROVED METHODS FOR THE RADICAL DECARBOXYLATION OF ACIDS
BARTON, DHR
CRICH, D
MOTHERWELL, WB
[J]. 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
BARTON, DHR
GERO, SD
QUICLETSIRE, B
SAMADI, M
[J]. 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
BARTON, DHR
HERVE, Y
POTIER, P
THIERRY, J
[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
BARTON, DHR
GUILHEM, J
HERVE, Y
POTIER, P
THIERRY, J
[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
BARTON, DHR
TOGO, H
ZARD, SZ
[J]. TETRAHEDRON, 1985, 41 (23) : 5507 - 5516
[7] REDUCTIVE RADICAL DECARBOXYLATION OF AMINO-ACIDS AND PEPTIDES
BARTON, DHR
HERVE, Y
POTIER, P
THIERRY, J
[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)
BARTON, DHR
OZBALIK, N
VACHER, B
[J]. TETRAHEDRON, 1988, 44 (12) : 3501 - 3512
[9] SYNTHESIS OF DISULFIDES VIA SULFENYLATION OF ALKYL AND ARYLDITHIOPYRIDINE N-OXIDES
BARTON, DHR
CHEN, C
WALL, GM
[J]. 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
BARTON, DHR
CRICH, D
HERVE, Y
POTIER, P
THIERRY, J
[J]. TETRAHEDRON, 1985, 41 (19) : 4347 - 4357

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