Reactions of 3-(Polyfluoroacyl)chromenones
with Heterocyclic Amines: Novel Synthesis of Polyfluoroalkyl-Containing
Fused Pyridines

Anton Kotljarov; Viktor O. Iaroshenko; Dmitriy M. Volochnyuk; Roman A. Irgashev; Vyacheslav Ya. Sosnovskikh

doi:10.1055/s-0029-1216995

PAPER

Reactions of 3-(Polyfluoroacyl)chromenones with Heterocyclic Amines: Novel Synthesis of Polyfluoroalkyl-Containing Fused Pyridines

Anton Kotljarov^a,b, Viktor O. Iaroshenko*^c,d, Dmitriy M. Volochnyuk^c, Roman A. Irgashev^e, Vyacheslav Ya. Sosnovskikh^e
^a Formaly Fachbereich Chemie der Universität Konstanz, Fach M-720, Universitätsstr. 10, 78457 Konstanz, Germany
^b Institute of Organic and Bioorganic Chemistry, University of Tartu, Jakobi 2, 50014 Tartu, Estonia
^c Enamine Ltd., 23 A. Matrosova st., 01103 Kyiv, Ukraine
Fax: +380(44)5373253; e-Mail: yaroshenko@enamine.net;
^d National Taras Shevchenko University, 62 Volodymyrska st., 01033 Kyiv 33, Ukraine
^e Department of Chemistry, Ural State University, 51 Lenina Ave., 620083 Ekaterinburg, Russian Federation

Abstract

Alle Artikel dieser Rubrik

Abstract

The selectivity of the reactions of 3-(polyfluoroacyl)-4H-chromen-4-ones with a wide range of aminoheterocycles and arylamines has been evaluated. The method described facilitates access to polyfluoroalkyl-containing fused pyridines.

Key words

aminoheterocycles - arylamines - condensation - chroman-4-ones - polyfluoroalkyl - fused pyridines

Volltext

Referenzen

References

<A NAME="RP07409SS-1A">1a</A> Al-Shaar AHM. Gilmour DW. Lythgoe DJ. McClenaghan I. Ramsden CA. J. Chem. Soc., Chem. Commun. 1989, 551

<A NAME="RP07409SS-1B">1b</A> Al-Shaar AHM. Gilmour DW. Lythgoe DJ. McClenaghan I. Ramsden CA. J. Chem. Soc., Perkin Trans. 1 1992, 2779

<A NAME="RP07409SS-1C">1c</A> Al-Shaar AHM. Chambers RK. Gilmour DW. Lythgoe DJ. McClenaghan I. Ramsden CA. J. Chem. Soc., Perkin Trans. 1 1992, 2789

<A NAME="RP07409SS-1D">1d</A> Allegretti M. Anacardio R. Cesta MC. Curti R. Mantovanini M. Nano G. Topai A. Zampella G. Org. Process Res. Dev. 2003, 7: 209

<A NAME="RP07409SS-1E">1e</A> Dang Q. Gomez-Galeno JE. J. Org. Chem. 2002, 67: 8703

<A NAME="RP07409SS-2A">2a</A> Isobe Y, Ogita H, Tobe M, Takahisa H, Matsui H, and Tomisawa H. inventors; JP 11,180,982.

<A NAME="RP07409SS-2B">2b</A> Silhar P. Pohl R. Votruba I. Hocek M. Org. Biomol. Chem. 2005, 3: 3001

<A NAME="RP07409SS-2C">2c</A> Oe T, Sueoka H, and Terasawa M. inventors; JP 62,010,085.

<A NAME="RP07409SS-3A">3a</A> Sakaguchi O, Takeshita M, and Izumi T. inventors; JP 2004,217,582.

<A NAME="RP07409SS-3B">3b</A> Lerner A, and Tiwari S. inventors; WO 2006,062,817.

<A NAME="RP07409SS-3C">3c</A> Germeyer S, Meade MCJ, Meissner H, Morschhaeuser G, Pairet M, Pestel S, Pieper MP, Pohl G, Reichl R, and Speck G. inventors; WO 2005,013,967.

<A NAME="RP07409SS-3D">3d</A> Warner JM. inventors; WO 2004,067,006.

<A NAME="RP07409SS-3E">3e</A> Bourguignon JJ. Desaubry L. Raboisson P. Wermuth CG. Lugnier C. J. Med. Chem. 1997, 40: 1768

<A NAME="RP07409SS-4A">4a</A> Iaroshenko VO. Volochnyuk DM. Wang Y. Vovk MV. Boiko VJ. Rusanov EB. Groth UM. Tolmachev AO. Synthesis 2007, 3309

<A NAME="RP07409SS-4B">4b</A> Iaroshenko VO. Wang Y. Sevenard DV. Volochnyuk DM. Synthesis 2009, 1851

<A NAME="RP07409SS-4C">4c</A> Iaroshenko VO. Sevenard DV. Volochnyuk DM. Wang Y. Martiloga A. Tolmachev AO. Synthesis 2009, 1865

<A NAME="RP07409SS-4D">4d</A> Volochnyuk DM. Pushechnikov AO. Krotko DG. Sibgatulin DA. Kovalyova SA. Tolmachev AA. Synthesis 2003, 1531

<A NAME="RP07409SS-4E">4e</A> Iaroshenko VO. Sevenard DV. Kotljarov A. Volochnyuk DM. Tolmachev AO. Sosnovskikh VYa. Synthesis 2009, 731

<A NAME="RP07409SS-5A">5a</A> Ryabukhin SV. Plaskon AS. Volochnyuk DM. Pipko SE. Tolmachev AA. Heterocycles 2008, 75: 583

<A NAME="RP07409SS-5B">5b</A> Randhavane PV. Kale SB. Jagdhani SG. Karale BK. Indian J. Heterocycl. Chem. 2007, 17: 153

<A NAME="RP07409SS-5C">5c</A> Sonawane SA. Karale BK. Shingare MS. Indian J. Heterocycl. Chem. 2004, 14: 155

<A NAME="RP07409SS-6A">6a</A> Plaskon AS. Ryabukhin SV. Volochnyuk DM. Gavrilenko KS. Shivanyuk AN. Tolmachev AA. J. Org. Chem. 2008, 73: 6010

<A NAME="RP07409SS-6B">6b</A> Ryabukhin SV. Plaskon AS. Volochnyuk DM. Tolmachev AA. Synthesis 2007, 1861

<A NAME="RP07409SS-6C">6c</A> Iaroshenko VO. Groth U. Kryvokhyzha NV. Obeid S. Tolmachev AA. Wesch T. Synlett 2008, 343

<A NAME="RP07409SS-7">7</A> Sosnovskikh VYa. Irgashev RA. Barabanov MA. Synthesis 2006, 2707

<A NAME="RP07409SS-8A">8a</A> Sosnovskikh VYa. Irgashev RA. Kodess MI. Tetrahedron 2008, 64: 2997

<A NAME="RP07409SS-8B">8b</A> Sosnovskikh VYa. Khalymbadzha IA. Irgashev RA. Slepukhin PA. Tetrahedron 2008, 64: 10172

<A NAME="RP07409SS-8C">8c</A> Sosnovskikh VYa. Irgashev RA. Khalymbadzha IA. Slepukhin PA. Tetrahedron Lett. 2007, 48: 6297

<A NAME="RP07409SS-9">9</A> Sosnovskikh VYa. Moshkin VS. Kodess MI. Tetrahedron 2008, 64: 7877

Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 721116 for 3n, CCDC 721117 for 4a, and CCDC 721118 for 5g can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 (1223)336033; e-mail: deposit@ccdc.cam.ac.uk].