Facile Synthesis of Steroidal [16,17-c]Tetrahydropyridazine Derivatives by One-Pot Stille Coupling and Hetero-Diels-Alder Reactions

Rita Skoda-Földes; László Kollár

doi:10.1055/s-2006-942517

PAPER

Facile Synthesis of Steroidal [16,17-c]Tetrahydropyridazine Derivatives by One-Pot Stille Coupling and Hetero-Diels-Alder Reactions

Rita Skoda-Földes*^a, László Kollár^b
^a University of Veszprém, Department of Organic Chemistry and Research Group for Petrochemistry of the Hungarian Academy of Sciences, Egyetem u. 8., P. O. Box 158, 8200 Veszprém, Hungary
Fax: +36(88)624469; e-Mail: skodane@almos.vein.hu;
^b University of Pécs, Department of Inorganic Chemistry and Research Group for Chemical Sensors of the Hungarian Academy of Sciences, Ifjúság u. 6., P. O. Box 266, 7624 Pécs, Hungary

Abstract

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Abstract

The synthesis of new steroidal [16,17-c]tetrahydropyridazine derivatives as mixtures of 16α- and 16β-isomers has been accomplished by consecutive Stille coupling and hetero-Diels-Alder reactions. The products were obtained in a one-pot reaction without the isolation of the diene intermediates.

Key words

cycloadditions - Stille reaction - steroids - palladium - annulations

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References

<A NAME="RT05206SS-1">1</A> Loozen HJJ. inventors; Eur. Pat. Appl. EP 0869132. ; Chem. Abstr. 1998, 129, 2760957

<A NAME="RT05206SS-2">2</A> Gupta R. Pathak D. Jindal DP. Eur. J. Med. Chem. 1996, 31: 241

<A NAME="RT05206SS-3">3</A> Kwon T. Heiman AS. Oriaku ET. Yoon K. Lee HJ. J. Med. Chem. 1995, 38: 1048

<A NAME="RT05206SS-4">4</A> Laitonjam WS. Rajkumar TS. Chingakham BS. Steroids 2002, 67: 203

<A NAME="RT05206SS-5">5</A> Siddiqui AU. Rao VUM. Maimirani M. Siddiqui AH. J. Heterocycl. Chem. 1995, 32: 353

<A NAME="RT05206SS-6">6</A> Forgó P. Vincze I. Steroids 2002, 67: 749

<A NAME="RT05206SS-7">7</A> Matsumoto T. Watanabe M. Mataka S. Thiemann T. Steroids 2003, 68: 751

<A NAME="RT05206SS-8">8</A> Chowdhury P. Das AM. Goswami P. Steroids 2005, 70: 494

<A NAME="RT05206SS-9">9</A> Watanabe M. Mataka S. Thiemann T. Steroids 2005, 70: 856

<A NAME="RT05206SS-10">10</A> Yoshizawa J. Tomoeda M. J. Chem. Soc. C 1971, 1741

<A NAME="RT05206SS-11">11</A> Skoda-Földes R. Jeges G. Kollár L. Horváth J. Tuba Z. Tetrahedron Lett. 1996, 37: 2085

<A NAME="RT05206SS-12">12</A> Skoda-Földes R. Jeges G. Kollár L. Horváth J. Tuba Z. J. Org. Chem. 1997, 62: 1326

<A NAME="RT05206SS-13">13</A> Skoda-Földes R. Vándor K. Kollár L. Horváth J. Tuba Z. J. Org. Chem. 1999, 64: 5921

<A NAME="RT05206SS-14">14</A> De Riccardis F. Meo D. Izzo I. Di Filippo M. Casapullo A. Eur. J. Org. Chem. 1998, 1965

<A NAME="RT05206SS-15">15</A> Jeges G. Skoda-Földes R. Kollár L. Horváth J. Tuba Z. Tetrahedron 1998, 54: 6767

<A NAME="RT05206SS-16">16</A> Jeges G. Skoda-Földes R. Kollár L. Pintér Z. Horváth J. Tuba Z. J. Mol. Catal. A: Chem. 2001, 165: 89

<A NAME="RT05206SS-17">17</A> Skoda-Földes R. Csákai Z. Kollár L. Horváth J. Tuba Z. Steroids 1995, 60: 812