Convenient preparation of substituted 5-aminooxazoles via a microwave-assisted Cornforth rearrangement

被引：21

作者：

Nolt, MB ^{[1
]}

Smiley, MA ^{[1
]}

Varga, SL ^{[1
]}

McClain, RT ^{[1
]}

Wolkenberg, SE ^{[1
]}

Lindsley, CW ^{[1
]}

机构：

[1] Merck & Co Inc, Dept Med Chem, Technol Enabled Synth Grp, Merck Res Labs, West Point, PA 19486 USA

来源：

TETRAHEDRON | 2006年 / 62卷 / 19期

关键词：

D O I：

10.1016/j.tet.2005.12.065

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The preparation of oxazole-4-carboxam ides and their subsequent thermal rearrangement to 5-aminooxazole-4-carboxylates is optimized in a high-speed microwave-assisted procedure. The reaction sequence is effective with a variety of substituted oxazoles, and produces products in good yield and high purity. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：4698 / 4704

页数：7

共 30 条

[1] Suzuki coupling of aryl chlorides with phenylboronic acid in water, using microwave heating with simultaneous cooling [J].

Arvela, RK ;

Leadbeater, NE .

ORGANIC LETTERS, 2005, 7 (11) :2101-2104

[2] The chemistry of pseudomonic acid .15. Synthesis and antibacterial activity of a series of 5-alkyl, 5-alkenyl, and 5-heterosubstituted oxazoles [J].

Brown, P ;

Davies, DT ;

OHanlon, PJ ;

Wilson, JM .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (02) :446-457

[3] Rapid synthesis of α-ketoamides using microwave irradiation-simultaneous cooling method [J].

Chen, JJ ;

Deshpande, SV .

TETRAHEDRON LETTERS, 2003, 44 (49) :8873-8876

[4] CHEMISTRY OF PSEUDOMONIC ACID .2. CONVERSION OF PSEUDOMONIC ACID-A INTO MONIC ACID-A AND ITS ESTERS [J].

CLAYTON, JP ;

LUK, K ;

ROGERS, NH .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (02) :308-313

[5] HETEROCYCLIZATION OF ALPHA ACYLAMINOAMIDES .4. MECHANISMS FOR OPENING AND FORMATION OF 5-AMINOOXAZOLE CYCLE [J].

CLERIN, D ;

KILLE, G ;

FLEURY, JP .

TETRAHEDRON, 1974, 30 (03) :469-474

[6] FUNCTIONALIZED OXAZOLES FROM RHODIUM-CATALYZED REACTION OF DIMETHYL DIAZOMALONATE WITH NITRILES [J].

CONNELL, R ;

SCAVO, F ;

HELQUIST, P ;

AKERMARK, B .

TETRAHEDRON LETTERS, 1986, 27 (46) :5559-5562

[7] THE CHEMISTRY OF PSEUDOMONIC ACID .2. DEHYDRATIVE CYCLIZATION OF ALPHA-ACYLAMINO KETONES TO OXAZOLES [J].

CRIMMIN, MJ ;

OHANLON, PJ ;

ROGERS, NH ;

SIME, FM ;

WALKER, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (11) :2059-2063

[8] THE CHEMISTRY OF PSEUDOMONIC ACID .10. PREPARATION OF HETEROCYCLIC-DERIVATIVES [J].

CRIMMIN, MJ ;

OHANLON, PJ ;

ROGERS, NH ;

WALKER, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (11) :2047-2057

[9] NATURE OF INTERMEDIATE IN CORNFORTH REARRANGEMENT [J].

DEWAR, MJS ;

SPANNING.PA ;

TURCHI, IJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1973, (24) :925-926

[10] INVESTIGATION OF SCOPE AND LIMITATIONS OF CORNFORTH REARRANGEMENT [J].

DEWAR, MJS ;

TURCHI, IJ .

JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (10) :1521-1523

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