One-pot synthesis of 2-aminothiazoles using supported reagents

被引：42

作者：

Kodomari, M ^{[1
]}

Aoyama, T ^{[1
]}

Suzuki, Y ^{[1
]}

机构：

[1] Shibaura Inst Technol, Dept Appl Chem, Minato Ku, Tokyo 1088548, Japan

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 09期

关键词：

D O I：

10.1016/S0040-4039(02)00084-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and efficient method has been developed for the synthesis of 2-aminothiazoles from alpha-bromo ketones in one-pot using a supported reagents system, KSCN/SiO2-RNH3OAc/Al2O3, in which alpha-bromo ketone reacts first with KSCN/SiO2 and the product, alpha-thiocyano ketone, reacts with RNH3OAc/Al2O3 to give the final product, 2-aminothiazole, in high yield. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：1717 / 1720

页数：4

共 12 条

[1] A convenient procedure for the solution phase preparation of 2-aminothiazole combinatorial libraries [J].

Bailey, N ;

Dean, AW ;

Judd, DB ;

Middlemiss, D ;

Storer, R ;

Watson, SP .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (12) :1409-1414

[2] WOLF AND LAMB REACTIONS - EQUILIBRIUM AND KINETIC EFFECTS IN MULTIPOLYMER SYSTEMS [J].

COHEN, BJ ;

KRAUS, MA ;

PATCHORNIK, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (25) :7620-7629

[3] N-(4-SUBSTITUTED-THIAZOLYL)OXAMIC ACID-DERIVATIVES, A NEW SERIES OF POTENT, ORALLY ACTIVE ANTIALLERGY AGENTS [J].

HARGRAVE, KD ;

HESS, FK ;

OLIVER, JT .

JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (08) :1158-1163

[4] 3-[1-(2-BENZOXAZOLYL)HYDRAZINO]PROPANENITRILE DERIVATIVES - INHIBITORS OF IMMUNE-COMPLEX INDUCED INFLAMMATION [J].

HAVIV, F ;

RATAJCZYK, JD ;

DENET, RW ;

KERDESKY, FA ;

WALTERS, RL ;

SCHMIDT, SP ;

HOLMS, JH ;

YOUNG, PR ;

CARTER, GW .

JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (09) :1719-1728

[5] Solid-phase synthesis of 2-aminothiazoles [J].

Kearney, PC ;

Fernandez, M ;

Flygare, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (01) :196-200

[6] VACILLATING REACTIONS [J].

KIM, B ;

REGEN, SL .

TETRAHEDRON LETTERS, 1983, 24 (07) :689-690

[7]

KODOMARI M, 1983, SYNTHESIS-STUTTGART, P141

[8] STRUCTURE-ACTIVITY-RELATIONSHIPS OF A SERIES OF 2-AMINO-4-THIAZOLE-CONTAINING RENIN INHIBITORS [J].

PATT, WC ;

HAMILTON, HW ;

TAYLOR, MD ;

RYAN, MJ ;

TAYLOR, DG ;

CONNOLLY, CJC ;

DOHERTY, AM ;

KLUTCHKO, SR ;

SIRCAR, I ;

STEINBAUGH, BA ;

BATLEY, BL ;

PAINCHAUD, CA ;

RAPUNDALO, ST ;

MICHNIEWICZ, BM ;

OLSON, SC .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (14) :2562-2572

[9] Facile access to N-thiazolyl α-amino acids from α-bromo ketones and α-amino acids [J].

Rudolph, J .

TETRAHEDRON, 2000, 56 (20) :3161-3165

[10] Expedient synthesis of N-substituted 2-aminothiazoles [J].

Schantl, JG ;

Lagoja, IM .

SYNTHETIC COMMUNICATIONS, 1998, 28 (08) :1451-1462

← 1 2 →