Synthetic Access to New Pyridone Derivatives through the Alkylation Reactions of Hydroxypyridines with Epoxides

References

• Guimon , C. , Garrabe , G. and Pfister‐Guillouzo , G. 1979 . Application of photoelectronic spectroscopy to molecular properties, 7: Photoelectronic spectroscopy at various temperatures—Prototropic equilibrium of 2‐hydroxypyridine and 2‐mercaptopyridine . Tetrahedron Lett. , 28 : 2585 – 2588 .
   Google Scholar
• Hatherley , L. D. , Brown , R. D. , Godfrey , P. D. , Pierlot , A. P. , Caminati , W. , Damiani , D. , Merlandi , S. and Favero , L. B. 1993 . Gas‐phase tautomeric equilibrium of 2‐pyridinone and 2‐hydroxypyridine by microwave spectroscopy . J. Phys. Chem. , 97 ( 1 ) : 46 – 51 .
   Web of Science ®Google Scholar
• Nowak , M. J. , Lapinski , L. , Fulara , J. , Less , A. and Adamovicz , L. 1992 . Matrix‐isolation IR spectroscopy of tautomeric systems and its theoretical interpretation, 2: Hydroxypyridine/2(1H)‐pyridinone . J. Phys. Chem. , 96 ( 4 ) : 1562 – 1569 .
   Web of Science ®Google Scholar
• Dkhissi , A. , Houben , L. , Smets , J. , Adamovicz , L. and Maes , G. 1999 . Density functional theory and ab initio computational study of the 2‐hydroxypyridine/2‐pyridone system: A comparison with FT‐IR data from matrix isolation experiments . J. Mol. Struct. , 484 ( 1–3 ) : 215 – 227 .
   Google Scholar
• Schlegel , H. B. , Gund , P. and Fluder , E. M. 1982 . Tautomerization of formamide, 2‐pyridone, and 4‐pyridone—An ab initio study . J. Am. Chem. Soc. , 104 ( 20 ) : 5347 – 5351 .
   Web of Science ®Google Scholar
• Field , M. J. , Hillier , I. H. and Guest , M. F. 1984 . Equilibrium and activation energetics, and molecular structures in the water‐catalyzed lactim lactam tautomerism of 2‐pyridone—An ab initio molecular‐orbital study . J. Chem. Soc., Chem. Commun. , 19 : 1310 – 1311 .
   Google Scholar
• Chou , P. T. , Wei , C. Y. and Hung , F. T. 1997 . Conjugated dual hydrogen bonds mediating 2‐pyridone/2‐hydroxypyridine tautomerism . J. Phys. Chem. B , 101 ( 44 ) : 9119 – 9126 .
   Web of Science ®Google Scholar
• Beak , P. 1977 . Energies and alkylations of tautomeric heterocyclic‐compounds—Old problems new answers . Acc. Chem. Res. , 10 ( 5 ) : 186 – 192 .
   Web of Science ®Google Scholar
• Tsuchida , N. and Yamabe , S. 2005 . Reaction paths of tautomerization between hydroxypyridines and pyridones . J. Phys. Chem. A , 109 ( 9 ) : 1974 – 1980 .
   PubMed Web of Science ®Google Scholar
• Dou , H. J.‐M. , Hassanaly , P. and Metzger , J. 1977 . Alkylation of ambident anions in phase transfer catalysis—Example of hydroxypyridines . J. Heterocycl. Chem. , 14 ( 2 ) : 321 – 323 .
   Web of Science ®Google Scholar
• Johnson , B. L. , Kitahara , Y. , Weakley , T. J. R. and Keana , J. F. W. 1993 . Intramolecular [2+2] photocycloaddition of juxtaposed 4‐pyridone moieties . Tetrahedron Lett. , 34 ( 35 ) : 5555 – 5558 .
   Web of Science ®Google Scholar
• You , F. and Twieg , R. J. 1999 . Aromatic nucleophilic substitution with 4‐hydroxypyridine . Tetrahedron Lett. , 40 ( 50 ) : 8759 – 8762 .
   Web of Science ®Google Scholar
• Stefanuti , I. , Smith , S. A. and Taylor , R. J. K. 2000 . Unsaturated enamides via organometallic addition to isocyanates: The synthesis of lansamide‐I, lansiumamides A‐C and SB‐204900 . Tetrahedron Lett. , 41 ( 19 ) : 3735 – 3738 .
   Web of Science ®Google Scholar
• Gentili , D. , Lapucci , A. , Macchia , B. , Macchia , M. , Martinelli , A. , Nencetti , S. , Orlandeni , E. , Ferni , G. and Pinza , M. 1995 . Synthesis and beta‐adrenergic activity of a series of 3‐(substituted‐benzylideneaminoxy)propanolamine derivatives . Il Farmaco , 50 ( 7–8 ) : 519 – 526 .
   PubMedGoogle Scholar
• Desideri , N. , Sestili , I. , Manarini , S. , Cerletti , C. and Stein , M. L. 1991 . Guanylhydrazones of 3‐substituted 2‐pyridinecarboxaldehyde and of (2‐substituted 3‐pyridinyloxy) acetaldehyde as prostanoid biosynthesis and platelet‐aggregation inhibitors . Eur. J. Med. Chem. , 26 ( 4 ) : 455 – 460 .
   Web of Science ®Google Scholar
• Manna , F. , Bolasco , A. , Bizzari , B. and Lena , R. 1996 . Synthesis and beta‐adrenoreceptor blocking activity of [[3‐(alkylamine)‐2‐hydroxypropyl]oximino]pyredines and O[3(alkylamine)‐2‐hydroxypropyl]methylpyridine ketone oximes derivatives . Il Farmaco , 51 ( 8–9 ) : 579 – 587 .
   PubMedGoogle Scholar
• Dondas , H. A. and Yaktubay , N. 2003 . N‐Heterocycles from oxime and oxime o‐benzyl ethers via electrophile induced‐ring formation: Route to cyclic and bicyclic amine and hydroxylamine . Heterocycl. Commun. , 9 ( 1 ) : 23 – 30 .
   Google Scholar
• Hopkins , G. C. , Jonak , J. P. , Tieckelmann , H. and Minnemeyer , H. J. 1966 . Alkylations of heterocyclic amibident anions 1: 2‐Hydroxypyrimidines . J. Org. Chem. , 31 ( 12 ) : 3969
   Google Scholar
• Meialich , H. 1962 . Pyridine and its Derivatives, Part III Edited by: Klingsberg , E. 631 New York : Interscience .
   Google Scholar
• Kornblum , N. , Smiley , R. A. , Blackwood , R. K. and Iffiand , D. C. 1955 . The chemistry of aliphatic and alicyclic nitro compounds, 9: The mechanism of the reaction of silver nitrite with alkyl halides—The contrasting reactions of silver and alkali metal salts with alkyl halides—The alkylation of ambident anions . J. Am. Chem. Soc. , 77 ( 23 ) : 6269 – 6280 .
   Google Scholar
• Looker , J. H. , Prokop , R. J. , Serbousek , W. E. and Cliffton , M. D. 1979 . Bromomaltol—Structure and conversion to novel pyridone and pyridine derivatives . J. Org. Chem. , 44 ( 19 ) : 3408 – 3410 .
   Web of Science ®Google Scholar
• Busch‐Petersen , J. and Corey , E. J. 2000 . A rhodium(II) catalytic approach to the synthesis of ethers of a minor component in a tautomeric set . Org. Lett. , 2 ( 11 ) : 1641 – 1643 .
   PubMedGoogle Scholar
• Mabic , S. and Castagnoli , N. 1996 . Selective reductions of 1‐methyl‐4‐phenyl‐2‐pyridone . J. Org. Chem. , 61 ( 1 ) : 309 – 313 .
   Web of Science ®Google Scholar
• Kurbanli , S. , Sen , N. , Guler , E. and Kocak , A. 2004 . The investigation of the alkylation reactions of hydroxyl and En‐oximes with some halohydrins and epoxides . Synth. Commun. , 34 ( 9 ) : 1663 – 1675 .
   Web of Science ®Google Scholar
• Kurbanli , S. , Kocak , A. and Malkondu , S. 2007 . O‐Alkylation of pyridine aldo‐and ketoximes with dihalohydrins under phase‐transfer conditions . Synth. Commun. , 37 ( 7 ) : 1155 – 1165 .
   Web of Science ®Google Scholar
• Knunyantz , I. L. 1935 . Condensations of aliphatic oxides with α‐aminopyridine . Ber. , 68B : 397 – 399 .
   Google Scholar
• Shepherd , R. G. , Bratton , A. C. and Blanchard , K. C. 1942 . Properties of the nitrogen‐carbon‐nitrogen system in N1‐heterocyclic sulfanilamides . J. Am. Chem. Soc. , 64 : 2532 – 2537 .
   Google Scholar
• Somekawa , K. , Okuhira , H. , Sendayama , M. , Suishu , T. and Shimo , T. 1992 . Intramolecular [2+2]photocycloadditions of 1‐(ω‐alkenyl)‐2‐pyridones possessing an ester group on the olefinic carbon chain . J. Org. Chem. , 57 ( 21 ) : 5708 – 5712 .
   Web of Science ®Google Scholar
• Mariano , P. S. , Krochmal , E. , Beamer , R. , Huesmann , P. L. and Mariano‐Dunaway , D. 1978 . General synthetic methods for the preparation of 1‐substituted‐vinyl‐2‐pyridones . Tetrahedron , 34 ( 17 ) : 2609 – 2616 .
   Web of Science ®Google Scholar
• Moehrle , H. and Ottersbach , D. 1990 . “ Sodium mercury EDTA dehydrogenation of N‐aliphatic‐substituted 1,2,3,6‐tetrahydropyridine derivatives ” . In Arc. Pharm. Vol. 323 , 109 – 115 . Weinheim, , Germany 2
   Google Scholar
• Gray , A. P. , Heitmeier , D. E. and Spinner , E. E. 1959 . Aminopyridines, II: The preparation and properties of 2‐(hydroxyalkylamino)pyridines . J. Am. Chem. Soc. , 81 : 4351 – 4355 .
   Google Scholar