A Novel, Facile, Simple and Convenient Oxidative Aromatization of Hantzsch 1,4-Dihydropyridines to Pyridines Using Polymeric Iodosobenzene with KBr

被引：13

作者：

Kumar, Parvin ^{[1
]}

机构：

[1] Guru Nanak Khalsa Coll, Dept Chem, Yamunanagar, India

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2010年 / 47卷 / 06期

关键词：

OXYGEN-ATOM TRANSFER; EFFICIENT OXIDATION; MEDIATED OXIDATION; HYPERVALENT IODINE; CARBONYL-COMPOUNDS; NITRIC-OXIDE; CHEMISTRY; NAD(P)H; ANTAGONISTS; METABOLISM;

D O I：

10.1002/jhet.504

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An easy, safe, effective and handy method for oxidative aromatization of Hantzsch 1,4-dihydropyridines catalyzed by hypervalent iodine (iodosobenzene) and potassium bromide to corresponding pyridine derivatives in high-yields and within short span of time was described. Dealkylation in case of 4-n-alkyl substituted I,4-dihydropyridines was not obtained.

引用

页码：1429 / 1433

页数：5

共 60 条

[1] Chemoselective C-H oxidation of alcohols to carbonyl compounds with iodosobenzene catalyzed by (salen)chromium complex [J].

Adam, W ;

Gelalcha, FG ;

Saha-Möller, CR ;

Stegmann, VR .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (07) :1915-1918

[2] 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

[3] FREE-RADICAL SCAVENGING AND INHIBITION OF LIPID-PEROXIDATION BY BETA-BLOCKERS AND BY AGENTS THAT INTERFERE WITH CALCIUM-METABOLISM - A PHYSIOLOGICALLY-SIGNIFICANT PROCESS [J].

ARUOMA, OI ;

SMITH, C ;

CECCHINI, R ;

EVANS, PJ ;

HALLIWELL, B .

BIOCHEMICAL PHARMACOLOGY, 1991, 42 (04) :735-743

[4] Microwave-assisted oxidative aromatization of Hantzsch 1,4-dihydropyridines using manganese dioxide [J].

Bagley, MC ;

Lubinu, MC .

SYNTHESIS-STUTTGART, 2006, (08) :1283-1288

[5] 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

[6] REACTIVITY OF BIOLOGICALLY IMPORTANT REDUCED PYRIDINES .4. EFFECT OF SUBSTITUTION ON FERRICYANIDE-MEDIATED OXIDATION RATES OF VARIOUS 1,4-DIHYDROPYRIDINES [J].

BREWSTER, ME ;

SIMAY, A ;

CZAKO, K ;

WINWOOD, D ;

FARAG, H ;

BODOR, N .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (15) :3721-3726

[7] 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

[8] Hypervalent iodine in synthesis. 76. An efficient oxidation of 1,4-dihydropyridines to pyridines using iodobenzene diacetate [J].

Cheng, DP ;

Chen, ZC .

SYNTHETIC COMMUNICATIONS, 2002, 32 (05) :793-798

[9] Copper-catalyzed nitrogen transfer mediated by iodosylbenzene PhI=O [J].

Dauban, P ;

Sanière, L ;

Tarrade, A ;

Dodd, RH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (31) :7707-7708

[10] UNUSUAL OXIDATIVE DEALKYLATION OF CERTAIN 4-ALKYL-1,4-DIHYDROPYRIDINES WITH MNO2/BENTONITE USING MICROWAVE IRRADIATION, IN THE ABSENCE OF SOLVENT(II) [J].

DELGADO, F ;

ALVAREZ, C ;

GARCIA, O ;

PENIERES, G ;

MARQUEZ, C .

SYNTHETIC COMMUNICATIONS, 1991, 21 (21) :2137-2141

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