Microwave-assisted oxidative aromatization of Hantzsch 1,4-dihydropyridines using manganese dioxide

被引：83

作者：

Bagley, MC ^{[1
]}

Lubinu, MC ^{[1
]}

机构：

[1] Univ Cardiff Wales, Sch Chem, Cardiff CF10 3AT, Wales

来源：

SYNTHESIS-STUTTGART | 2006年 / 08期

关键词：

aromatization; Hantzsch dihydropyridines; heterocycles; microwave synthesis; oxidation;

D O I：

10.1055/s-2006-926407

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

4-Aryl- and 4-alkyl-1,4-dihydropyridines, prepared by microwave-assisted Hantzsch reaction, are readily and efficiently aromatized in only one minute using commercial manganese dioxide in the absence of an inorganic support at 100 degrees C under microwave irradiation. This rapid procedure is more efficient than microwave-assisted arornatization using Pd/C, iodine or o-iodoxy-benzoic acid (IBX) and gives the dehydrogenated or 4-dealkylated product in 91-100% yield (13 examples).

引用

收藏

页码：1283 / 1288

页数：6

相关论文

共 56 条

[1] THE REDUCTION OF THIOKETONES BY A MODEL FOR A COENZYME [J].

ABELES, RH ;

HUTTON, RF ;

WESTHEIMER, FH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (03) :712-716

[2] SYNTHESIS OF 1,4-DIHYDROPYRIDINES UNDER MICROWAVE IRRADIATION [J].

ALAJARIN, R ;

VAQUERO, JJ ;

NAVIO, JLG ;

ALVAREZBUILLA, J .

SYNLETT, 1992, (04) :297-298

[3] MNO2 BENTONITE - A NEW REACTIVE FOR THE OXIDATION OF HANTZSCH DIHYDROPYRIDINES USING MICROWAVE IRRADIATION, IN THE ABSENCE OF SOLVENT .1. [J].

ALVAREZ, C ;

DELGADO, F ;

GARCIA, O ;

MEDINA, S ;

MARQUEZ, C .

SYNTHETIC COMMUNICATIONS, 1991, 21 (05) :619-624

[4] Synthesis of Hantzsch 1,4-dihydropyridines under microwave irradiation [J].

Anniyappan, M ;

Muralidharan, D ;

Perumal, PT .

SYNTHETIC COMMUNICATIONS, 2002, 32 (04) :659-663

[5] A novel application of the oxidizing properties of urea nitrate and peroxydisulfate-cobalt(II): aromatization of NAD(P)H model Hantzsch 1,4-dihydropyridines [J].

Anniyappan, M ;

Muralidharan, D ;

Perumal, PT .

TETRAHEDRON, 2002, 58 (25) :5069-5073

[6] CLAY-SUPPORTED REAGENT - AROMATIZATION OF 1,4-DIHYDROPYRIDINES BY CLAY-SUPPORTED METAL NITRATES [J].

BALOGH, M ;

HERMECZ, I ;

MESZAROS, Z ;

LASZLO, P .

HELVETICA CHIMICA ACTA, 1984, 67 (08) :2270-2272

[7] ELECTROCHEMICAL OXIDATION OF NADH ANALOGS [J].

BLAEDEL, WJ ;

HAAS, RG .

ANALYTICAL CHEMISTRY, 1970, 42 (08) :918-+

[8]

BOCKER RH, 1986, J MED CHEM, V29, P1596

[9] An efficient Co(II) catalyzed auto oxidation of 1,4-dihydropyridines [J].

Chavan, SP ;

Kharul, RK ;

Kalkote, UR ;

Shivakumar, I .

SYNTHETIC COMMUNICATIONS, 2003, 33 (08) :1333-1340

[10] An efficient oxidation of 1,4-dihydropyridines using aqueous tert.-butylhydroperoxide [J].

Chavan, SP ;

Dantale, SW ;

Kalkote, UR ;

Jyothirmai, VS ;

Kharul, RK .

SYNTHETIC COMMUNICATIONS, 1998, 28 (15) :2789-2792

← 1 2 3 4 5 6 →