Synthesis of Substituted Phenyl 2-Aminopyridine-3-sulfonates

Abstract

A series of phenyl 2-aminopyridine-3-sulfonates 3 has been synthesized starting from phenyl cyanomethanesulfonate (5). Pinner reaction with 5 gave phenoxysulfonylketene aminal 4K which was cyclocondensed with a series of C₃-biselectrophiles to yield the title compounds, which are of pharmaceutical and medicinal interest.

Key words

pyridines - condensation - tautomerisation - phenoxysulfonylketene aminals - 2-aminopyridine-3-sulfonates

References

• 1 Yale HL. Sheehan JT. J. Org. Chem.  1991,  26:  4315 
• 2 Weller HN. Miller AV. Moquin RV. Dickinson KEJ. Hedberg SA. Moreland S. Cohen RB. Delaney CL. Skwish S. Williams S. Bioorg. Med. Chem. Lett.  1992,  2:  1115 
• 3 Pirotte B. de Tullio P. Lebrun P. Antoine M.-H. Fontaine J. Masereel B. Schynts M. Dupont L. Herchuelz A. Delarge J. J. Med. Chem.  1993,  36:  3211 
• 4 de Tullio P. Pirotte B. Dupont L. Masereel B. Laeckmann D. Podona T. Diouf O. Lebrun P. Delarge J. Tetrahedron  1995,  51:  3221 
• 5 Neill CG. Preston PN. Wightman RH. Tetrahedron  1998,  54:  13645 
• 6 Troschütz R. Arch. Pharm. (Weinheim, Ger.)  1979,  312:  455 
• 7 Söllhuber-Kretzer M. Troschütz R. Roth HJ. Arch. Pharm. (Weinheim, Ger.)  1982,  315:  199 
• 8 Mertens H. Troschütz R. Roth HJ. Arch. Pharm. (Weinheim, Ger.)  1986,  319:  380 
• 9 Troschütz R. Arch. Pharm. (Weinheim, Ger.)  1989,  322:  285 
• 10 Krutak JJ. Burpitt RD. Moore WH. Hyatt JA. J. Org. Chem.  1979,  44:  3847 
• 11 Hoogenboom BE. Abbott R. Locatell L. Hinman RL. J. Org.Chem.  1959,  24:  1983 
• 12 Bredereck H. Effenberger F. Botsch H. Chem. Ber.  1964,  97:  3397 
• 13 Pichler H. Folkers G. Roth HJ. Eger K. Liebigs Ann. Chem.  1986,  1485 
• 14 Troschütz R. Dennstedt T. Arch. Pharm (Weinheim, Ger.)  1994,  327:  221