Synthesis of Thiazolo[4,5-d]pyridines

Abstract

The reaction of 2-aminothiazol-4(5H)-iminium salts with various 1,3-CCC-dielectrophiles was investigated. As a result, a set of diverse thiazolo[4,5-d]pyridines were obtained. The scope and limitation of the approach is described.

Key words

thiazoles - pyridines - annulation - fluorine - diketones - regioselectivity

References

• 1a Tsushima M, Kano Y, Iwamatsu K, Tamura A, and Shibahara S. inventors; EP  0,605,836.  ; Chem. Abstr. 1995, 122, 31198
• 1b Sunagawa M, Yamaga H, Sumita Y, and Shinagawa H. inventors; WO  995,8536.  ; Chem. Abstr. 1999, 131, 336878
• 1c Katano K, Tomomoto T, Ogino H, Yamazaki N, Hirano F, Yuda Y, Konno F, Nishio M, Machinami T, Shibahara S, Tsuruoka T, and Inouye S. inventors; US  5,200,407.  ; Chem. Abstr. 1991, 114, 228904
• 1d Walczynski K. Zuiderveld OP. Timmerman H. Eur. J. Med. Chem.  2005,  40:  15 
• 2a Kulkarni SS. Newman AH. Bioorg. Med. Chem. Lett.  2007,  17:  2987 
• 2b Jouve K. Bergman J. J. Heterocycl. Chem.  2003,  40:  261 
• 2c Smith K. Anderson D. Matthews I. Sulfur Lett.  1995,  18:  79 
• 2d Couture A. Huguerre E. Grandclaudon P. Synth. Commun.  1989,  19:  713 
• 3a Johnson SG. Connolly PJ. Murray WV. Tetrahedron Lett.  2006,  47:  4853 
• 3b Gewald K. Rehwald M. Gruner M. Liebigs Ann. Chem.  1993,  5:  457 
• 3c Ismail NA. Khalifa FA. Fekry RM. Abdel AYN. Phosphorus, Sulfur Silicon Relat. Elem.  1992,  66:  29 
• 3d Hayakawa I. Tanaka Y. Heterocycles  1984,  22:  1697 
• 4a Flaig R. Hartmann H. Monatsh. Chem.  1997,  128:  1051 
• 4b El-Desoky EI. Aboul-Fetouh S. Metwally MA. J. Chem. Technol. Biotechnol.  1996,  67:  153 
• 4c Komaritsa ID. Khim. Geterotsikl. Soedin.  1989,  11:  1547 
• For our previous work with aminoheterocycles see:
• 5a Volochnyuk DM. Pushecnikov AO. Krotko DG. Sibgatulin DA. Kovaleva SA. Tolmachev AA. Synthesis  2003,  1531 
• 5b Volochnyuk DM. Kostyuk AN. Pinchuk AM. Tolmachev AA. Tetahedron Lett.  2003,  44:  391 
• 5c Pushechnikov AO. Volochnyuk DM. Tolmachev AA. Synlett  2002,  1040 
• 5d Vovk MV. Bol’but AV. Volochnyuk DM. Pinchuk AM. Russ. J. Org. Chem.  2004,  40:  63 
• 5e Ryabukhin SV. Plaskon AS. Volochnyuk DM. Tolmachev AA. Synthesis  2007,  1861 
• 5f Iaroshenko VO. Volochnyuk DM. Wang Y. Vovk MV. Boiko VJ. Rusanov EB. Groth UM. Tolmachev AO. Synthesis  2007,  3309 
• 6 Flaig R. Hartmann H. J. Heterocycl. Chem.  1997,  34:  1291 
• 7a Yokoyama M. Kurauchi M. Imamoto T. Tetrahedron Lett.  1981,  22:  2285 
• 7b Kikelj D. Urleb U. Science of Synthesis   Vol. 11:  Schaumann E. Georg Thieme Verlag; Stuttgart: 2002.  p.627 
• 8a Nayyar A. Malde A. Jain R. Coutinho E. Bioorg. Med. Chem.  2006,  14:  847 
• 8b Schmieden V. Jezequel S. Betz H. Mol. Pharmacol.  1996,  50:  1200 
• 8c Vaitilingam B. Nayyar A. Palde PB. Monga V. Jain R. Kaur S. Singh PP. Bioorg. Med. Chem.  2004,  12:  4179 
• 8d Batt DG. Copeland RA. Dowling RL. Gardner TL. Jones EA. Orwat MJ. Pinto DJ. Pitts WJ. Magolda RL. Jaffee BD. Bioorg. Med. Chem. Lett.  1995,  5:  1549 

9

Sheldrick G. M. SHELXTL PLUS. PC Version. A system of computer programs for the determination of crystal structure from X-ray diffraction data. Rev.5.1. 1998.

10

Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Center as supplementary publications CCDC 677236 and 677237 and can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: [phone]; e-mail: [e-mail].