A new synthesis of 3,4-disubstituted 1,2,5-thiadiazoles

被引：5

作者：

Biju, Purakkattle ^{[1
]}

Yu, Younong ^{[1
]}

机构：

[1] Schering Plough Res Inst, Kenilworth, NJ 07033 USA

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 30期

关键词：

2,5-thiadiazole 1-oxide; 1,2,5-thiadiazole; triphenylphosphine and carbon tetrachloride;

D O I：

10.1016/j.tetlet.2007.05.123

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and convenient reduction of 3,4-diamino derivatives of 2,5-thiadiazole-1-oxide to the corresponding 1,2,5-thiadiazoles has been accomplished using Ph(3)P and CCl(4) in dichloromethane. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：5279 / 5282

页数：4

共 15 条

[1] 1,2,5-THIADIAZOLE 1-OXIDE AND 1,1-DIOXIDE DERIVATIVES - A NEW CLASS OF POTENT HISTAMINE H2-RECEPTOR ANTAGONISTS [J].

ALGIERI, AA ;

LUKE, GM ;

STANDRIDGE, RT ;

BROWN, M ;

PARTYKA, RA ;

CRENSHAW, RR .

JOURNAL OF MEDICINAL CHEMISTRY, 1982, 25 (03) :210-212

[2] 1,2,5-THIADIAZOLE 1-OXIDES .3. AN EXPERIMENTAL AND THEORETICAL INVESTIGATION OF THE INVERSION BARRIER [J].

AMATO, JS ;

KARADY, S ;

REAMER, RA ;

SCHLEGEL, HB ;

SPRINGER, JP ;

WEINSTOCK, LM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (05) :1375-1380

[3] Discovery of 2-hydroxy-N,N-dimethyl-3-{2-[[(R)-1-(5-methylfuran-2-yl)propyl]amino]-3,4-dioxocyclobut-1-enylamino}benzamide (SCH 527123):: A potent, orally bioavailable CXCR2/CXCR1 receptor antagonist [J].

Dwyer, Michael P. ;

Yu, Younong ;

Chao, Jianping ;

Aki, Cynthia ;

Chao, Jianhua ;

Biju, Purakkattle ;

Girijavallabhan, Viyyoor ;

Rindgen, Diane ;

Bond, Richard ;

Mayer-Ezel, Rosemary ;

Jakway, James ;

Hipkin, R. William ;

Fossetta, James ;

Gonsiorek, Waldemar ;

Bian, Hong ;

Fan, Xuedong ;

Terminelli, Carol ;

Fine, Jay ;

Lundell, Daniel ;

Merritt, J. Robert ;

Rokosz, Laura L. ;

Kaiser, Bernd ;

Li, Ge ;

Wang, Wei ;

Stauffer, Tara ;

Ozgur, Lynne ;

Baldwin, John ;

Taveras, Arthur G. .

JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (26) :7603-7606

[4] TIMOLOL DERIVATIVES .1. X-RAY, NMR AND THEORETICAL-STUDIES OF THE CRYSTALLIZATION OF (S)-TIMOLOL O,O-DIACETYL-L-TARTARIC ACID MONOESTER [J].

KIVIKOSKI, J ;

VEPSALAINEN, J ;

SUONTAMO, R ;

POHJALA, E ;

LAATIKAINEN, R .

TETRAHEDRON-ASYMMETRY, 1993, 4 (04) :709-722

[5] Chemistry of 4-dicyanomethylene-1,2,6-thiadiazines [J].

Koutentis, PA ;

Rees, CW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (07) :1081-1088

[6] Synthesis and structure-activity relationships of 3,4-diaminocyclobut-3-ene-1,2-dione CXCR2 antagonists [J].

Merritt, J. Robert ;

Rokosz, Laura L. ;

Nelson, Kingsley H., Jr. ;

Kaiser, Bernd ;

Wang, Wei ;

Stauffer, Tara M. ;

Ozgur, Lynne E. ;

Schilling, Adriane ;

Li, Ge ;

Baldwin, John J. ;

Taveras, Arthur G. ;

Dwyer, Michael P. ;

Chao, Jianping .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (15) :4107-4110

[7] CLONING OF COMPLEMENTARY-DNA ENCODING A FUNCTIONAL HUMAN INTERLEUKIN-8 RECEPTOR [J].

MURPHY, PM ;

TIFFANY, HL .

SCIENCE, 1991, 253 (5025) :1280-1283

[8] SYNTHESIS AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF ALKYL SUBSTITUTED ANALOGS OF THE FUNCTIONAL M(1) SELECTIVE MUSCARINIC RECEPTOR AGONIST XANOMELINE [J].

QUIMBY, SJ ;

SHANNON, HE ;

BYMASTER, FP ;

SAUERBERG, P ;

OLESEN, PH ;

SHEARDOWN, MJ ;

SUZDAK, PD ;

MITCH, CH .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (18) :2205-2210

[9] NOVEL FUNCTIONAL-M1 SELECTIVE MUSCARINIC AGONISTS - SYNTHESIS AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF 3-(1,2,5-THIADIAZOLYL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRIDINES [J].

SAUERBERG, P ;

OLESEN, PH ;

NIELSEN, S ;

TREPPENDAHL, S ;

SHEARDOWN, MJ ;

HONORE, T ;

MITCH, CH ;

WARD, JS ;

PIKE, AJ ;

BYMASTER, FP ;

SAWYER, BD ;

SHANNON, HE .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (12) :2274-2283

[10] Comparison of the ocular beta-blockers [J].

Sorensen, SJ ;

Abel, SR .

ANNALS OF PHARMACOTHERAPY, 1996, 30 (01) :43-54

← 1 2 →