Superelectrophilic Activation in Superacid HF/SbF5 and Synthesis of Benzofused Sultams

被引：43

作者：

Liu, Fei ^{[1
]}

Martin-Mingot, Agnes ^{[1
]}

Jouannetaud, Marie-Paule ^{[1
]}

Zunino, Fabien ^{[2
]}

Thibaudeau, Sebastien ^{[1
]}

机构：

[1] Lab Synth & React Subst Nat, UMR 6514, F-86022 Poitiers, France

[2] RtMolecule, F-86022 Poitiers, France

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 04期

关键词：

CARBONIC-ANHYDRASE INHIBITORS; MEDICINAL CHEMISTRY; INTRAMOLECULAR CARBOAMINATION; SULFONAMIDES; HF-SBF5; FLUORINE; PROTONATION; MECHANISM; ALKENES; SITE;

D O I：

10.1021/ol9029287

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of benzofused sultams and/or fluorinated sulfonamides, starting from N-allylic sulfonamides, was performed in superacid HF/SbF5, through superelectrophilic activation. A dramatic effect of superacid composition on the selectivity of the reaction was shown and applied to the synthesis of cyclic 4-aminobenzenesulfonamides.

引用

页码：868 / 871

页数：4

共 41 条

[1]

[Anonymous], 2000, HDB HETEROCYCLIC CHE

[2]

Bagno A, 1999, CHEM-EUR J, V5, P523, DOI 10.1002/(SICI)1521-3765(19990201)5:2<523::AID-CHEM523>3.0.CO

[3]

2-1

[4] Recent advances (1995-2005) in fluorinated pharmaceuticals based on natural products [J].

Begue, Jean-Pierre ;

Bonnet-Delpon, Daniele .

JOURNAL OF FLUORINE CHEMISTRY, 2006, 127 (08) :992-1012

[5] Synthesis of α-fluoro- and α,α-difluoro-benzenemethanesulfonamides:: new inhibitors of carbonic anhydrase [J].

Blackburn, GM ;

Türkmen, H .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (02) :225-226

[6] IONIC SPECIES IN HF-SBF5 SOLUTIONS - INFRARED-SPECTROSCOPY INVESTIGATION [J].

BONNET, B ;

MASCHERPA, G .

INORGANIC CHEMISTRY, 1980, 19 (03) :785-788

[7] Stereoselective synthesis of homochiral annulated sultams via intramolecular cycloaddition reactions [J].

Chiacchio, U ;

Corsaro, A ;

Rescifina, A ;

Bkaithan, M ;

Grassi, G ;

Piperno, A ;

Privitera, T ;

Romeo, G .

TETRAHEDRON, 2001, 57 (16) :3425-3433

[8] Fluoroanions and cations in the HF-SbF5 superacid system.: A 19F and 1H NMR study [J].

Culmann, JC ;

Fauconet, M ;

Jost, R ;

Sommer, J .

NEW JOURNAL OF CHEMISTRY, 1999, 23 (08) :863-867

[9] HYDROCARBON OXIDATION BY ANTIMONY PENTAFLUORIDE [J].

CULMANN, JC ;

SOMMER, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (10) :4057-4058

[10] 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

← 1 2 3 4 5 →