INTRAMOLECULAR AMINOLYSIS OF 2′-AMINOCHALCONE EPOXIDES USING InBr3 OR BiCl3 AS EFFICIENT CATALYSTS

被引：10

作者：

Ahmed, Naseem ^{[1
]}

Kumar, Harendra ^{[1
]}

Babu, B. Venkata ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Roorkee 247667, Uttar Pradesh, India

来源：

SYNTHETIC COMMUNICATIONS | 2013年 / 43卷 / 04期

关键词：

2 '-Aminochalcones/epoxides; aminolysis; 2-aryl-3-hydroxy-2,3-dihydro-4-quinolones; epoxidering opening; metal halides; ANTITUMOR AGENTS; CORRESPONDING 2-ARYL-2,3-DIHYDROQUINOLIN-4(1H)-ONES; BIOLOGICAL EVALUATION; CHALCONES; OXIDATION; FACILE; 2-PHENYL-4-QUINOLONES; CYCLIZATION; FLAVANONES; ALCOHOLS;

D O I：

10.1080/00397911.2011.604571

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the synthesis of aza-flavanone derivatives, several metal halides were screened for their catalytic activity. Among them, BiCl3 and InBr3 catalyze the ring opening of 2'-aminochalcone epoxides followed by intramolecular aminolysis under mild conditions. The reactions proceed efficiently at room temperature to afford highly functionalized 2-aryl-3-hydroxy-2,3-dihydro-4-quinolones (aza-flavanones) in excellent yields (82-92%). Intermolecular aminolysis of 2'-aminochalcone epoxides with aniline derivatives failed under the same catalytic conditions.

引用

页码：567 / 581

页数：15

共 30 条

[1] Silica gel supported TaBr5:: new catalyst for the facile and rapid cyclization of 2′-aminochalcones to the corresponding 2-aryl-2,3-dihydroquinolin-4(1H)-ones under solvent-free conditions [J].

Ahmed, N ;

van Lier, JE .

TETRAHEDRON LETTERS, 2006, 47 (16) :2725-2729

[2] Silica gel supported InBr3 and InCl3:: new catalysts for the facile and rapid oxidation of 2′-hydroxychalcones and flavanones to their corresponding flavones under solvent free conditions [J].

Ahmed, N ;

Ali, H ;

van Lier, JE .

TETRAHEDRON LETTERS, 2005, 46 (02) :253-256

[3]

Ahmed N, 2003, J CHEM RES-S, P572

[4] The reaction of porphyrins with α,β-acetylenic ketone/ester (Morita-Baylis-Hiliman) promoted by MgI2 and subsequent Sonogashira coupling reactions [J].

Ahmed, Naseem ;

Ali, Hasrat ;

van Lier, Johan E. .

JOURNAL OF PORPHYRINS AND PHTHALOCYANINES, 2006, 10 (9-10) :1172-1178

[5] Alumina supported-CeCl3•7H2O-NaI:: an efficient catalyst for the cyclization f 2′-aminochalcones to the corresponding 2-aryl-2,3-dihydroquinolin-4(1H)-ones under solvent free conditions [J].

Ahmed, Naseem ;

van Lier, Johan E. .

TETRAHEDRON LETTERS, 2007, 48 (01) :13-15

[6] Molecular iodine in isopropenyl acetate (IPA): a highly efficient catalyst for the acetylation of alcohols, amines and phenols under solvent free conditions [J].

Ahmed, Naseem ;

van Lier, Johan E. .

TETRAHEDRON LETTERS, 2006, 47 (30) :5345-5349

[7] EPOXIDATION OF ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS BY DIMETHYLDIOXIRANE [J].

BAUMSTARK, AL ;

HARDEN, DB .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (26) :7615-7618

[8]

Beifuss U, 1998, SYNLETT, P649

[9] 'Metal ion electrophilic catalysis' in ring-opening reactions of 1,2-epoxides by metal halides in ionic liquids [J].

Betti, Cecilia ;

Landini, Dario ;

Maia, Angelamaria .

SYNLETT, 2006, (09) :1335-1338

[10]

CHAWLA HM, 1990, TETRAHEDRON, V46, P1611

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