IBX/TEAB-mediated oxidative dimerization of thioamides: synthesis of 3,5-disubstituted 1,2,4-thiadiazoles

被引：60

作者：

Patil, Pravin C. ^{[1
]}

Bhalerao, Dinesh S. ^{[1
]}

Dangate, Prasad S. ^{[1
]}

Akamanchi, Krishnacharya G. ^{[1
]}

机构：

[1] Inst Chem Technol, Dept Pharmaceut Sci & Technol, Bombay 400019, Maharashtra, India

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 42期

关键词：

Hypervalent iodine reagents; o-Iodoxybenzoic acid; TEAB; Thioamides; Thiadiazoles; NITRILE; MILD; ACID;

D O I：

10.1016/j.tetlet.2009.07.155

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Thioamides undergo oxidative dimerization on treatment with hypervalent iodine(V)-containing reagents, particularly o-iodoxybenzoic acid (IBX), in the presence of tetraethylammonium bromide (TEAB) to generate 3,5-disubstituted 1,2,4-thiadiazoles in excellent yield. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：5820 / 5822

页数：3

共 27 条

[1] Direct oxidative conversion of aldehydes to nitriles using IBX in aqueous ammonia [J].

Arote, Nitin D. ;

Bhalerao, Dinesh S. ;

Akamanchi, Krishnacharya G. .

TETRAHEDRON LETTERS, 2007, 48 (21) :3651-3653

[2] Oxidative Conversion of α,α-Disubstituted Acetamides to Corresponding One-Carbon-Shorter Ketones Using Hypervalent Iodine (λ5) Reagents in Combination with Tetraethylammonium Bromide [J].

Bellale, Eknath V. ;

Bhalerao, Dinesh S. ;

Akamanchi, Krishnacharya G. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (23) :9473-9475

[3] Oxidative bromination of aromatic compounds using O-iodoxybenzoic acid with tetraethylammonium bromide [J].

Bhalerao, Dinesh S. ;

Mahajan, Ulhas S. ;

Akamanchi, Krishnacharya G. .

SYNTHETIC COMMUNICATIONS, 2008, 38 (16) :2814-2819

[4] o-Iodoxybenzoic acid- and tetraethylammonium bromide-mediated oxidative transformation of primary carboxamides to one-carbon dehomologated nitriles [J].

Bhalerao, Dinesh S. ;

Mahajan, Ulhas S. ;

Chaudhari, Kiran H. ;

Akamanchi, Krishnacharya G. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (02) :662-665

[5] Novel and facile transformation of N,N-Disubstituted glycylamides into corresponding cyanamides by using pentavalent iodine reagents in combination with tetraethylammonium bromide [J].

Chaudhari, Kiran H. ;

Mahajan, Ulhas S. ;

Bhalerao, Dinesh S. ;

Akamanchi, Krishnacharya G. .

SYNLETT, 2007, (18) :2815-2818

[6] Hypervalent iodine in synthesis. 84. Facile synthesis of 3,5-disubstituted 1,2,4-thiadiazoles by oxidative dimerization of thioamides using polymer-supported iodobenzene diacetate [J].

Cheng, DP ;

Chen, ZC .

SYNTHETIC COMMUNICATIONS, 2002, 32 (14) :2155-2159

[7]

Craig E. M., 1980, U.S. Patent, Patent No. [4209522, 4,209,522]

[8] THE REACTION OF NITROUS ACID WITH THIOBENZAMIDES [J].

CRONYN, MW ;

NAKAGAWA, TW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (14) :3693-3693

[9] THE REACTION OF TERT-BUTYL HYPOCHLORITE WITH THIOCARBONYL COMPOUND - A CONVENIENT METHOD FOR THE GREATER-THANC=S-]GREATER-THANC=O TRANSFORMATION [J].

ELWASSIMY, MTM ;

JORGENSEN, KA ;

LAWESSON, SO .

TETRAHEDRON, 1983, 39 (10) :1729-1734

[10] NITRILE SULFIDES - SYNTHESIS OF 1,2,4-THIADIAZOLES [J].

HOWE, RK ;

FRANZ, JE .

JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (07) :962-964

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