An efficient combination of Dess-Martin periodinane with molecular iodine or KBr for the facile oxidative aromatization of Hantzsch 1,4-dihydropyridines

被引：13

作者：

Karade, Nandkishor N. ^{[1
]}

Gampawar, Sumeet V. ^{[1
]}

Kondre, Jeevan M. ^{[1
]}

Shinde, Sandeep V. ^{[1
]}

机构：

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

来源：

ARKIVOC | 2008年

关键词：

1,4-Dihydropyridines; hypervalent iodine; Dess-Martin periodinane; oxidation; molecular iodine; potassium bromide; acetyl hypoiodite;

D O I：

10.3998/ark.5550190.0009.c02

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient, mild, and simple protocol is presented for the oxidative aromatization of Hantzsch 1, 4-dihydropyridines using the combination of Dess-Martin periodinane with molecular iodine or KBr. The in situ generated acetyl hypoiodite or bromite formed due to the reaction between Dess-Martin periodinane and molecular iodine or KBr respectively is supposed to be the responsible species for bringing about the oxidative aromatization of 1, 4dihydropyridines.

引用

页码：9 / 16

页数：8

共 66 条

[1] A convenient and efficient protocol for oxidative aromatization of Hantzsch 1,4-dihydropyridines using benzyltriphenylphosphonium peroxymonosulfate under almost neutral reaction conditions [J].

Adibi, Hadi ;

Hajipour, Abdol Reza .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (04) :1008-1012

[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]

[Anonymous], [No title captured]

[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] Instability of calcium channel antagonists during sample preparation for LC-MS-MS analysis of serum samples [J].

Baranda, AB ;

Alonso, RM ;

Jiménez, RM ;

Weinmann, W .

FORENSIC SCIENCE INTERNATIONAL, 2006, 156 (01) :23-34

[7]

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

[8] (Diacetoxyiodo)benzene-lithium bromide as a convenient electrophilic Br+ source [J].

Braddock, DC ;

Cansell, G ;

Hermitage, SA .

SYNLETT, 2004, (03) :461-464

[9]

BUHLER FR, 1987, J HYPERTENS, V5, pS3

[10] Aromatization of 1,4-dihydropyridines with selenium dioxide [J].

Cai, XH ;

Yang, HJ ;

Zhang, GL .

CANADIAN JOURNAL OF CHEMISTRY, 2005, 83 (03) :273-275

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