A highly efficient procedure for 3-sulfenylation of indole-2-carboxylates

被引：155

作者：

Schlosser, KM ^{[1
]}

Krasutsky, AP ^{[1
]}

Hamilton, HW ^{[1
]}

Reed, JE ^{[1
]}

Sexton, K ^{[1
]}

机构：

[1] Pfizer Global Res & Dev, Dept Chem, Ann Arbor, MI 48105 USA

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 05期

关键词：

D O I：

10.1021/ol049956v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient one-pot procedure for 3-sulfenylation of 2-carboxyindoles is described. Treatment of thiols with N-chlorosuccinimide at -78 degreesC in CH2Cl2 affords sulfenyl chlorides in situ that readily react with 2-carboxyindoles to give 3-thioindoles in high yields. This new method is milder, produces less waste, and is compatible with a wide range of thiol and indole functionality.

引用

页码：819 / 821

页数：3

共 18 条

[1] ALKYLTHIATION AND ARYLTHIATION OF URACIL AND INDOLE
ANZAI, K
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1979, 16 (03) : 567 - 569
[2] SYNTHESIS OF 3-(ALKYL AND ARYL)THIO-2-ISOCEPHEMS
ASZODI, J
CHANTOT, JF
COLLARD, J
TEUTSCH, G
[J]. HETEROCYCLES, 1989, 28 (02) : 1061 - 1076
[3] ATKINSON JG, 1988, SYNTHESIS-STUTTGART, P480
[4] Berger J. P., 2001, [No title captured], Patent No. [WO0130343, 0130343]
[5] Berryman K. A., 1996, U.S. Patent, Patent No. [5,482,960, 5482960]
[6] THIOMETHYLATION OF INDOLE AND HALOINDOLE ZINC SALTS
BROWDER, CC
MITCHELL, MO
SMITH, RL
ELSULAYMAN, G
[J]. TETRAHEDRON LETTERS, 1993, 34 (39) : 6245 - 6246
[7] 1-Benzyl-3-thioaryl-2-carboxyindoles as potent non-peptide endothelin antagonists
Bunker, AM
Edmunds, JJ
Berryman, KA
Walker, DM
Flynn, MA
Welch, KM
Doherty, AM
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (12) : 1367 - 1370
[8] HAMILTON HW, 2002, Patent No. 60400092
[9] Resin-immobilised benzyl and aryl vinyl sulfones: New versatile traceless linkers for solid-phase organic synthesis
Kroll, FEK
Morphy, R
Rees, D
Gani, D
[J]. TETRAHEDRON LETTERS, 1997, 38 (49) : 8573 - 8576
[10] CONVERSION OF INDOLE INTO 3-S-(CYSTEINYL)INDOLES AND 2-S-(CYSTEINYL)TRYPTOPHANS - AN APPROACH TO TRYPTATHIONINES
PLATE, R
NIVARD, RJF
OTTENHEIJM, HCJ
[J]. TETRAHEDRON, 1986, 42 (16) : 4503 - 4509

← 1 2 →