PREPARATION AND UTILITY OF DIANIONS FROM N-TERT-BUTYLTHIOPHENE-2-SULFONAMIDE

被引：37

作者：

GRAHAM, SL

SCHOLZ, TH

机构：

[1] Department of Medicinal Chemistry, Merck Sharp and Dohme Research Laboratories, West Point

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 13期

关键词：

D O I：

10.1021/jo00013a034

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Metalation of N-tert-butylthiophene-2-sulfonamide with n-butyllithium occurs competitively at the 3- and 5-position of the thiophene ring. Equilibration of the initial mixture of carbanions or metalation with lithium diisopropylamide allows selective formation of the N,5-dilithiothiophenesulfonamide 7. This dianion is useful for the preparation of a number of 5-substituted thiophene-2-sulfonamides.

引用

收藏

页码：4260 / 4263

页数：4

相关论文

共 21 条

[1]

BARNISH IT, Patent No. 1516024

[2] REGIOSELECTIVE ALPHA-METALLATIONS AND BETA-METALLATIONS OF THIOPHENE DERIVATIVES BEARING THE 4,4-DIMETHYLOXAZOLIN-2-YL GROUP - APPLICATION OF THE METHOD TO SYNTHESES OF 2,3-DISUBSTITUTED AND 2,5-DISUBSTITUTED THIOPHENE DERIVATIVES [J].

CARPENTER, AJ ;

CHADWICK, DJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (01) :173-181

[3] THE SCOPE AND LIMITATIONS OF CARBOXAMIDE-INDUCED BETA-DIRECTED METALATION OF 2-SUBSTITUTED FURAN, THIOPHENE, AND 1-METHYLPYRROLE DERIVATIVES - APPLICATION OF THE METHOD TO SYNTHESES OF 2,3-DISUBSTITUTED THIOPHENES AND FURANS [J].

CARPENTER, AJ ;

CHADWICK, DJ .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (22) :4362-4368

[4] REGIOSELECTIVE BETA-METALLATIONS OF 2-SUBSTITUTED FURAN AND N-METHYLPYRROLE DERIVATIVES EMPLOYING THE DIRECTING EFFECT OF THE OXAZOLINO GROUP - SYNTHESES OF 2,3-DISUBSTITUTED FURANS AND N-METHYLPYRROLES [J].

CHADWICK, DJ ;

MCKNIGHT, MV ;

NGOCHINDO, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (06) :1343-1347

[5] LITHIATION OF HETEROCYCLES DIRECTED BY ALPHA-AMINO ALKOXIDES [J].

COMINS, DL ;

KILLPACK, MO .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (01) :104-109

[6] TOPICALLY ACTIVE CARBONIC-ANHYDRASE INHIBITORS .3. BENZOFURAN-SULFONAMIDE AND INDOLE-2-SULFONAMIDE [J].

GRAHAM, SL ;

HOFFMAN, JM ;

GAUTHERON, P ;

MICHELSON, SR ;

SCHOLZ, TH ;

SCHWAM, H ;

SHEPARD, KL ;

SMITH, AM ;

SMITH, RL ;

SONDEY, JM ;

SUGRUE, MF .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (02) :749-754

[7]

GRAHAM SL, 1986, SYNTHESIS-STUTTGART, P1031

[8] A NEW MODE OF REACTIVITY OF N-METHOXY-N-METHYLAMIDES WITH STRONGLY BASIC REAGENTS [J].

GRAHAM, SL ;

SCHOLZ, TH .

TETRAHEDRON LETTERS, 1990, 31 (44) :6269-6272

[9]

Gschwend H.W., 1979, ORG REACT, V26, P1

[10]

HOUSE HO, 1972, MODERN SYNTHETIC REA, P551