Cyanuric Chloride Catalysed Rapid Conversion of β-Ketoesters into β-Enaminoesters under Mild and Solvent-Free Conditions

被引：6

作者：

Kamble, V. T. ^{[1
]}

Joshi, N. S. ^{[1
]}

Atkore, S. T. ^{[1
]}

机构：

[1] Swami Ramanand Teerth Marathwada Univ, Sch Chem Sci, Organ Chem Res Lab, Nanded 431606, Maharashtra, India

来源：

JOURNAL OF THE IRANIAN CHEMICAL SOCIETY | 2011年 / 8卷 / 03期

关键词：

Amines; beta-Enaminoesters; beta-Ketoesters; Cyanuric chloride; CARBOXYLIC-ACIDS; AZA-ANNULATION; DIASTEREOSELECTIVE REDUCTION; CONVENIENT SYNTHESIS; ASYMMETRIC-SYNTHESIS; EFFICIENT SYNTHESIS; BLAISE REACTION; AMINO; ESTERS; DERIVATIVES;

D O I：

10.1007/BF03245892

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Cyanuric chloride is shown to be an extremely efficient catalyst for the synthesis of beta-enaminoesters from beta-ketoesters under solvent-free conditions by grinding in a mortar with pestle at 25 degrees C. A short reaction time, an inexpensive and easily available catalyst, mild reaction conditions and excellent yields of the products are attractive features of this methodology.

引用

页码：616 / 621

页数：6

共 60 条

[1] Asymmetric synthesis of nitrogen heterocycles by reaction of chiral β-enaminocarbonyl substrates with acrylate derivatives [J].

Agami, C ;

Dechoux, L ;

Hebbe, S .

TETRAHEDRON LETTERS, 2002, 43 (14) :2521-2523

[2] SYNTHESIS OF THE CARBAPENAM SYSTEM FROM GLUTAMIC-ACID AND ACETOACETIC ACID-DERIVATIVES [J].

BACHI, MD ;

BREIMAN, R ;

MESHULAM, H .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (09) :1439-1444

[3] Direct synthesis of 2-oxazolines from carboxylic acids using 2-chloro-4,6-dimethoxy-1,3,5-triazine under mild conditions [J].

Bandgar, BP ;

Pandit, SS .

TETRAHEDRON LETTERS, 2003, 44 (11) :2331-2333

[4] Highly rapid and direct synthesis of monoacylated piperazine derivatives from carboxylic acids under mild conditions [J].

Bandgar, BP ;

Pandit, SS .

TETRAHEDRON LETTERS, 2003, 44 (19) :3855-3858

[5] Synthesis of acyl azides from carboxylic acids using cyanuric chloride [J].

Bandgar, BP ;

Pandit, SS .

TETRAHEDRON LETTERS, 2002, 43 (18) :3413-3414

[6] ASYMMETRIC FORMATION OF QUATERNARY CENTERS THROUGH AZA-ANNULATION OF CHIRAL BETA-ENAMINO ESTERS WITH ACRYLATE DERIVATIVES [J].

BARTA, NS ;

BRODE, A ;

STILLE, JR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (14) :6201-6206

[7] Zn(ClO4)2•6H2O as a powerful catalyst for the conversion of β-ketoesters into β-enamino esters [J].

Bartoli, G ;

Bosco, M ;

Locatelli, M ;

Marcantoni, E ;

Melchiorre, P ;

Sambri, L .

SYNLETT, 2004, (02) :239-242

[8] A VERSATILE ROUTE TO BETA-ENAMINO ESTERS BY ACYLATION OF LITHIUM ENAMINES WITH DIETHYL CARBONATE OR BENZYL CHLOROFORMATE [J].

BARTOLI, G ;

CIMARELLI, C ;

DALPOZZO, R ;

PALMIERI, G .

TETRAHEDRON, 1995, 51 (31) :8613-8622

[9] CHEMOSELECTIVE AND DIASTEREOSELECTIVE REDUCTION OF BETA-ENAMINO ESTERS - A CONVENIENT SYNTHESIS OF BOTH CIS-GAMMA-AMINO AND TRANS-GAMMA-AMINO ALCOHOLS AND BETA-AMINO ESTERS [J].

BARTOLI, G ;

CIMARELLI, C ;

MARCANTONI, E ;

PALMIERI, G ;

PETRINI, M .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (18) :5328-5335

[10] Formation of dihydropyridone- and pyridone-based peptide analogs through aza-annulation of beta-enamino ester and amide substrates with alpha-amido acrylate derivatives [J].

Beholz, LG ;

Benovsky, P ;

Ward, DL ;

Barta, NS ;

Stille, JR .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (04) :1033-1042

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