Reactions of vinyl sulfone with α-diazo-β-ketosulfone and Bestmann-Ohira reagent for the regioselective synthesis of highly functionalized pyrazoles

被引：37

作者：

Kumar, Rahul ^{[1
]}

Nair, Deepa ^{[1
]}

Namboothiri, Irishi N. N. ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Bombay 400076, Maharashtra, India

来源：

TETRAHEDRON | 2014年 / 70卷 / 09期

关键词：

Pyrazoles; Bestmann-Ohira reagent; Diazosulfone; vinyl sulfone; BASE-MEDIATED REACTION; 1,3-DIPOLAR CYCLOADDITION; ASYMMETRIC-SYNTHESIS; BIOLOGICAL-ACTIVITY; CHEMISTRY; ANALOGS; DERIVATIVES; PHOSPHONYL; METAL; SULFONYLPYRAZOLES;

D O I：

10.1016/j.tet.2014.01.022

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 1,3-dipolar cycloaddition of diazomethylsulfone anion, generated in situ from alpha-diazo-beta-ketosulfone, with vinyl sulfone proceeds in a regioselective manner to provide sulfonylpyrazoles. Similar reaction of diazomethylphosphonate anion, derived from Bestmann-Ohira reagent, with vinyl sulfone leads to phosphonylpyrazoles. The sulfonyl group of vinyl sulfone undergoes chemoselective elimination in these reactions. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：1794 / 1799

页数：6

共 72 条

[1]

Alonso D.A., 2008, ORGANIC REACTIONS, V72, P367

[2] Cycloadditions and Cyclizations of Acetylenic, Allenic, and Conjugated Dienyl Sulfones [J].

Back, Thomas G. ;

Clary, Kristen N. ;

Gao, Detian .

CHEMICAL REVIEWS, 2010, 110 (08) :4498-4553

[3]

Bera K, 2013, J CHEM SCI, V125, P443, DOI 10.1007/s12039-013-0418-6

[4] Synthesis and structure of highly substituted pyrazole ligands and their complexes with platinum(II) and palladium(II) metal ions [J].

Budzisz, E ;

Malecka, M ;

Nawrot, B .

TETRAHEDRON, 2004, 60 (08) :1749-1759

[5] New methods in asymmetric catalysis based on new hemi-labile bidentate ligands [J].

Charette, Andr B. ;

Cote, Alexandre ;

Desrosiers, Jean-Nicolas ;

Bonnaventure, Isabelle ;

Lindsay, Vincent N. G. ;

Lauzon, Caroline ;

Tannous, Jad ;

Boezio, Alessandro A. .

PURE AND APPLIED CHEMISTRY, 2008, 80 (05) :881-890

[6] Celecoxib analogs possessing a N-(4-nitrooxybutyl)piperidin-4-yl or N-(4-nitrooxybutyl)-1,2,3,6-tetrahydropyridin-4-yl nitric oxide donor moiety: Synthesis, biological evaluation and nitric oxide release studies [J].

Chowdhury, Morshed A. ;

Abdellatif, Khaled R. A. ;

Dong, Ying ;

Yu, Gang ;

Huang, Zhangjian ;

Rahman, Moshfiqur ;

Das, Dipankar ;

Velazquez, Carlos A. ;

Suresh, Mavanur R. ;

Knaus, Edward E. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (04) :1324-1329

[7] Cascade Cyclization, Dipolar Cycloaddition to Bridged Tricyclic Amines Related to the Daphniphyllum Alkaloids [J].

Coldham, Iain ;

Burrell, Adam J. M. ;

Guerrand, Helene D. S. ;

Oram, Niall .

ORGANIC LETTERS, 2011, 13 (06) :1267-1269

[8] The annular tautomerism of the curcuminoid NH-pyrazoles [J].

Cornago, Pilar ;

Cabildo, Pilar ;

Claramunt, Rosa M. ;

Bouissane, Latifa ;

Pinilla, Elena ;

Torres, M. Rosario ;

Elguero, Jose .

NEW JOURNAL OF CHEMISTRY, 2009, 33 (01) :125-135

[9] Synthesis of functionalized tetrasubstituted pyrazolyl heterocycles - A review [J].

Dadiboyena, Sureshbabu ;

Nefzi, Adel .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (11) :5258-5275

[10] A Metal-Free, Aqueous and General Route to 1,5-Disubstituted-1,2,3-triazoles: 'Reversed Regioisomeric' 1,3-Dipolar Cycloaddition of Azides and Vinyl Sulfones [J].

Dey, Santu ;

Datta, Dhrubajyoti ;

Pathak, Tanmaya .

SYNLETT, 2011, (17) :2521-2524

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