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

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.

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

References

1a Al-Shaar AHM. Gilmour DW. Lythgoe DJ. McClenaghan I. Ramsden CA. J. Chem. Soc., Chem. Commun.  1989,  551 

1b Al-Shaar AHM. Gilmour DW. Lythgoe DJ. McClenaghan I. Ramsden CA. J. Chem. Soc., Perkin Trans. 1  1992,  2779 

1c Al-Shaar AHM. Chambers RK. Gilmour DW. Lythgoe DJ. McClenaghan I. Ramsden CA. J. Chem. Soc., Perkin Trans. 1  1992,  2789 

1d Allegretti M. Anacardio R. Cesta MC. Curti R. Mantovanini M. Nano G. Topai A. Zampella G. Org. Process Res. Dev.  2003,  7:  209 

1e Dang Q. Gomez-Galeno JE. J. Org. Chem.  2002,  67:  8703 

2a Isobe Y, Ogita H, Tobe M, Takahisa H, Matsui H, and Tomisawa H. inventors; JP  11,180,982. 

2b Silhar P. Pohl R. Votruba I. Hocek M. Org. Biomol. Chem.  2005,  3:  3001 

2c Oe T, Sueoka H, and Terasawa M. inventors; JP  62,010,085. 

3a Sakaguchi O, Takeshita M, and Izumi T. inventors; JP  2004,217,582. 

3b Lerner A, and Tiwari S. inventors; WO  2006,062,817. 

3c 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. 

3d Warner JM. inventors; WO  2004,067,006. 

3e Bourguignon JJ. Desaubry L. Raboisson P. Wermuth CG. Lugnier C. J. Med. Chem.  1997,  40:  1768 

4a Iaroshenko VO. Volochnyuk DM. Wang Y. Vovk MV. Boiko VJ. Rusanov EB. Groth UM. Tolmachev AO. Synthesis  2007,  3309 

4b Iaroshenko VO. Wang Y. Sevenard DV. Volochnyuk DM. Synthesis  2009,  1851 

4c Iaroshenko VO. Sevenard DV. Volochnyuk DM. Wang Y. Martiloga A. Tolmachev AO. Synthesis  2009,  1865 

4d Volochnyuk DM. Pushechnikov AO. Krotko DG. Sibgatulin DA. Kovalyova SA. Tolmachev AA. Synthesis  2003,  1531 

4e Iaroshenko VO. Sevenard DV. Kotljarov A. Volochnyuk DM. Tolmachev AO. Sosnovskikh VYa. Synthesis  2009,  731 

5a Ryabukhin SV. Plaskon AS. Volochnyuk DM. Pipko SE. Tolmachev AA. Heterocycles  2008,  75:  583 

5b Randhavane PV. Kale SB. Jagdhani SG. Karale BK. Indian J. Heterocycl. Chem.  2007,  17:  153 

5c Sonawane SA. Karale BK. Shingare MS. Indian J. Heterocycl. Chem.  2004,  14:  155 

6a Plaskon AS. Ryabukhin SV. Volochnyuk DM. Gavrilenko KS. Shivanyuk AN. Tolmachev AA. J. Org. Chem.  2008,  73:  6010 

6b Ryabukhin SV. Plaskon AS. Volochnyuk DM. Tolmachev AA. Synthesis  2007,  1861 

6c Iaroshenko VO. Groth U. Kryvokhyzha NV. Obeid S. Tolmachev AA. Wesch T. Synlett  2008,  343 

7 Sosnovskikh VYa. Irgashev RA. Barabanov MA. Synthesis  2006,  2707 

8a Sosnovskikh VYa. Irgashev RA. Kodess MI. Tetrahedron  2008,  64:  2997 

8b Sosnovskikh VYa. Khalymbadzha IA. Irgashev RA. Slepukhin PA. Tetrahedron  2008,  64:  10172 

8c Sosnovskikh VYa. Irgashev RA. Khalymbadzha IA. Slepukhin PA. Tetrahedron Lett.  2007,  48:  6297 

9 Sosnovskikh VYa. Moshkin VS. Kodess MI. Tetrahedron  2008,  64:  7877 

10

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: [phone]; e-mail: [e-mail]].