Synthesis of New 3-(1-Ethylsulfanyl-2-perfluoroalkyl)-5-hydroxy-5-methyl (or 5-phenyl)-1,5-dihydro-pyrrol-2-ones Starting from γ-Keto Thioesters and Amines

Jean-Philippe Bouillon; Bernard Tinant; Jean-Marc Nuzillard; Charles Portella

doi:10.1055/s-2004-815970

PAPER

Synthesis of New 3-(1-Ethylsulfanyl-2-perfluoroalkyl)-5-hydroxy-5-methyl (or 5-phenyl)-1,5-dihydro-pyrrol-2-ones Starting from γ-Keto Thioesters and Amines

Jean-Philippe Bouillon*^a, Bernard Tinant^b, Jean-Marc Nuzillard^c, Charles Portella^a
^a Laboratoire ‘Réactions Sélectives et Applications’, UMR CNRS 6519, Université de Reims, Faculté des Sciences B.P. 1039, 51687 Reims Cedex 2, France
Fax: +33(3)26913166; e-Mail: jp.bouillon@univ-reims.fr;
^b Université Catholique de Louvain, Laboratoire de Chimie Physique et de Cristallographie, 1 Place Louis Pasteur, 1348 Louvain-la-Neuve, Belgium
^c Laboratoire de Pharmacognoise, UMR CNRS 6013, Université de Reims, Faculté des Sciences, Batiment 18, Moulin de las Housse B. P. 1039, 51687 Reims Cedex 2, France

Abstract

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Abstract

γ-Keto thioesters were easily transformed into α,β-unsaturated lactams using a two-step process (via furans) or by a one-pot reaction. This methodology is general and efficient leading to a varied substitution pattern. The structures of all new heterocycles were assigned using 2D NMR experiments, computer-assisted elucidation, and X-ray diffraction analyses.

Key words

fluorine - nitrogen heterocycles - lactam - pyrrol-3-one

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References

<A NAME="RZ16403SS-1">1</A> Muzard M. Portella C. J. Org. Chem. 1993, 58: 29

<A NAME="RZ16403SS-2">2</A> Huot J.-F. Muzard M. Portella C. Synlett 1995, 247

<A NAME="RZ16403SS-3">3</A> Hénin B. Huot J.-F. Portella C. J. Fluorine Chem. 2001, 107: 281

<A NAME="RZ16403SS-4A">4a</A> Biomedicinal Aspects of Fluorine Compounds Filler R. Kobayashi Y. Elsevier; New York: 1982.

<A NAME="RZ16403SS-4B">4b</A> Welch JT. Tetrahedron 1987, 43: 3123

<A NAME="RZ16403SS-4C">4c</A> Fluorine in Bioorganic Chemistry Welch JT. Eswarakrishnan S. John Wiley & Sons; New York: 1991.

<A NAME="RZ16403SS-5A">5a</A> Hewitt CD. Silvester MJ. Aldrichimica Acta 1988, 21: 3

<A NAME="RZ16403SS-5B">5b</A> Differding E. Frick W. Lang RW. Martin P. Schmit C. Veenstra S. Greuter H. Bull. Soc. Chim. Belg. 1990, 99: 647

<A NAME="RZ16403SS-5C">5c</A> Silvester MJ. Aldrichimica Acta 1991, 24: 31

<A NAME="RZ16403SS-5D">5d</A> Silvester MJ. Aldrichimica Acta 1995, 28: 45

<A NAME="RZ16403SS-6">6</A> Brulé C. Bouillon J.-P. Nicolaï E. Portella C. Synthesis 2003, 436

<A NAME="RZ16403SS-7">7</A> Bouillon J.-P. Hénin B. Huot J.-F. Portella C. Eur. J. Org. Chem. 2002, 1556

<A NAME="RZ16403SS-8A">8a</A> Kurita J. Kojima H. Tsuchiya T. Heterocycles 1984, 22: 721

<A NAME="RZ16403SS-8B">8b</A> Iwasawa N. Maeyama K. J. Org. Chem. 1997, 62: 1918

<A NAME="RZ16403SS-8C">8c</A> Ghelfi F. Stevens CV. Laureyn I. Van Meenen E. Rogge TM. De Buyck L. Nikitin KV. Grandi R. Libertini E. Pagnoni UM. Schenetti L. Tetrahedron 2003, 59: 1147

<A NAME="RZ16403SS-8D">8d</A> Clark AJ. Dell CP. McDonagh JM. Geden J. Mawdsley P. Org. Lett. 2003, 5: 2063

<A NAME="RZ16403SS-8E">8e</A> Yeung BKS. Boger DL. J. Org. Chem. 2003, 68: 5249

<A NAME="RZ16403SS-9A">9a</A> Lightner DA. Low LK. J. Heterocycl. Chem. 1972, 9: 167

<A NAME="RZ16403SS-9B">9b</A> Arzoumanian H. Jean M. Nuel D. Garcia JL. Rosas N. Organometallics 1997, 16: 2726

<A NAME="RZ16403SS-10A">10a</A> Farina F. Martin MV. Paredes MC. Synthesis 1973, 167

<A NAME="RZ16403SS-10B">10b</A> Shiraki R. Sumino A. Tadano K.-I. Ogawa S. Tetrahedron Lett. 1995, 36: 5551

<A NAME="RZ16403SS-10C">10c</A> Kotera M. Roupioz Y. Defrancq E. Bourdat A.-G. Garcia J. Coulombeau C. Lhomme J. Chem.-Eur. J. 2000, 6: 4163

<A NAME="RZ16403SS-11">11</A> Nuzillard J.-M. Connolly JD. Delaude C. Richard B. Zèches-Hanrot M. Le Men-Olivier L. Tetrahedron 1999, 55: 11511

<A NAME="RZ16403SS-12">12</A> Spek A. PLATON: Molecular Geometry Program University of Utrecht; The Netherlands: 1998.

<A NAME="RZ16403SS-13">13</A> Bouillon J.-P. Didier B. Dondy B. Doussot P. Plantier-Royon R. Portella C. Eur. J. Org. Chem. 2001, 187

<A NAME="RZ16403SS-14">14</A> Sheldrick GM. SHELXS-97 and SHELXL-97: Program for the Solution and Refinement of Crystal Structures University of Göttingen; Germany: 1997.