Facile Synthesis of Steroidal
Primary Amides via Palladium-Catalyzed Aminocarbonylation
of Steroidal Alkenyl Halides

János Balogh; Sándor Mahó; Viktor Háda; László Kollár; Rita Skoda-Földes

doi:10.1055/s-2008-1067265

SHORTPAPER

Facile Synthesis of Steroidal Primary Amides via Palladium-Catalyzed Aminocarbonylation of Steroidal Alkenyl Halides

János Balogh^a, Sándor Mahó^b, Viktor Háda^b, László Kollár^c, Rita Skoda-Földes*^a
^a University of Pannonia, Institute of Chemistry, Department of Organic Chemistry, P. O. Box 158, 8201 Veszprém, Hungary
Fax: +36(88)624469; e-Mail: skodane@almos.uni-pannon.hu;
^b Chemical Works of Gedeon Richter Ltd., P.O. Box 27, 1475 Budapest 10, Hungary
^c University of Pécs, Department of Inorganic Chemistry, P. O. Box 266, 7624 Pécs, Hungary

Abstract

Alle Artikel dieser Rubrik

Abstract

A new method for the synthesis of primary amides from alkenyl iodides in one carbonylation step using ammonium carbamate as ammonia synthon is reported. The products were obtained in good yields under mild reaction conditions using CO (1-6 bar). Steroidal substrates with various moieties (e.g., 6-OH group, lactams, or aromatic A-ring) could be converted selectively into the products.

Key words

primary amides - carbonylations - steroids - palladium - homogeneous catalysis

Volltext

Referenzen

References

<A NAME="RT03808SS-1">1</A> Skoda-Földes R. Kollár L. Curr. Org. Chem. 2002, 6: 1097

<A NAME="RT03808SS-2">2</A> Schnyder A. Beller M. Mehltretter G. Nsenda T. Studer M. Indolese AF. J. Org. Chem. 2001, 66: 4311

<A NAME="RT03808SS-3">3</A> Ueda K. Sato Y. Mori M. J. Am. Chem. Soc. 2000, 122: 10722

<A NAME="RT03808SS-4">4</A> Wu X. Wannberg J. Larhed M. Tetrahedron 2006, 62: 4665

<A NAME="RT03808SS-5">5</A> Morera E. Ortar G. Tetrahedron Lett. 1998, 39: 2835

<A NAME="RT03808SS-6">6</A> Takács E. Varga C. Skoda-Földes R. Kollár L. Tetrahedron Lett. 2007, 48: 2453

<A NAME="RT03808SS-7">7</A> Zhu N. Ling Y. Lei X. Handratta V. Bdrodie AMH. Steroids 2003, 68: 603

<A NAME="RT03808SS-8A">8a</A> Amatore C. Carre E. Jutand A. M’Barki MA. Meyer G. Organometallics 1995, 14: 5605

<A NAME="RT03808SS-8B">8b</A> Csákai Z. Skoda-Földes R. Kollár L. Inorg. Chim. Acta 1999, 286: 93

<A NAME="RT03808SS-9">9</A> Skoda-Földes R. Takács E. Horváth J. Tuba Z. Kollár L. Green Chem. 2003, 5: 643

<A NAME="RT03808SS-10">10</A> Skoda-Földes R. Szarka Z. Kollár L. Dinya Z. Horváth J. Tuba Z. J. Org. Chem. 1999, 64: 2134

<A NAME="RT03808SS-11">11</A> Müller E. Péczely G. Skoda-Földes R. Takács E. Kokotos G. Bellis E. Kollár L. Tetrahedron 2005, 61: 797

<A NAME="RT03808SS-12">12</A> Skoda-Földes R. Csákai Z. Kollár L. Szalontai G. Horváth J. Tuba Z. Steroids 1995, 60: 786

<A NAME="RT03808SS-13">13</A> Skoda-Földes R. Székvölgyi Z. Kollár L. Berente Z. Horváth J. Tuba Z. Tetrahedron 2000, 56: 3415