Merging Cross-Metathesis and Radical Cyclization: A Straightforward Access to 4-Substituted Benzosultams

Sophie Feuillastre; Béatrice Pelotier; Olivier Piva

doi:10.1055/s-0032-1318147

Synthesis, Table of Contents

Synthesis 2013; 45(6): 810-816
DOI: 10.1055/s-0032-1318147

paper

Merging Cross-Metathesis and Radical Cyclization: A Straightforward Access to 4-Substituted Benzosultams

Sophie Feuillastre

Université de Lyon, Université Lyon 1, Institut de Chimie et de Biochimie Moléculaire et Supramoléculaire (ICBMS), UMR 5246 CNRS, Bat Raulin, 43 Bd. du 11 novembre 1918, 69622 Villeurbanne cedex, France Fax: +33(0)472448136 Email: piva@univ-lyon1.fr

,

Béatrice Pelotier

Université de Lyon, Université Lyon 1, Institut de Chimie et de Biochimie Moléculaire et Supramoléculaire (ICBMS), UMR 5246 CNRS, Bat Raulin, 43 Bd. du 11 novembre 1918, 69622 Villeurbanne cedex, France Fax: +33(0)472448136 Email: piva@univ-lyon1.fr

,

Olivier Piva*

Université de Lyon, Université Lyon 1, Institut de Chimie et de Biochimie Moléculaire et Supramoléculaire (ICBMS), UMR 5246 CNRS, Bat Raulin, 43 Bd. du 11 novembre 1918, 69622 Villeurbanne cedex, France Fax: +33(0)472448136 Email: piva@univ-lyon1.fr

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Abstract

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Abstract

N-Alkyl-N-allyl-2-bromobenzenesulfonamides were functionalized by selective E-cross-metathesis with various alkenes. Subsequent radical cyclization initiated by 2,2′-azobis(isobutyronitrile) and tris(trimethylsilyl)silane gave the corresponding 4-substituted benzosultams directly in moderate-to-good yields.

Key words

metathesis - cyclizations - radical reactions - sulfonamides - heterocycles

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References

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