Novel One-Pot Synthesis for 2,5-Diaryl and 5-Aryl-pyridazin-3(2H)-ones

REFERENCES

• Heinisch , G. ; Frank , H. Pharmacologically active pyridazine derivatives, part 1 . In Progress in Medicinal Chemistry ; G. P. Ellis , G. B. West (Eds.); Elsevier : Amsterdam , 1990 ; vol. 27 , pp. 1 – 49 .
   Google Scholar
• Heinisch , G. ; Frank , H. K. Pharmacologically active pyridazine derivatives, part 2 . In Progress in Medicinal Chemistry ; G. P. Ellis , G. B. West (Eds.); Elsevier : Amsterdam , 1992 ; vol. 29 , pp. 141 – 183 .
   Google Scholar
• Okushima , H. ; Narimatsu , A. ; Kobayashi , M. ; Furuya , R. ; Tsuda , K. ; Kitada , Y. A novel class of cardiotonics: Synthesis and pharmacological properties of [4-(substituted-amino)phenyl]pyridazinones and related derivatives . J. Med. Chem. 1987 , 30 , 1157 – 1161 .
   PubMed Web of Science ®Google Scholar
• Akahane , A. ; Katayama , H. ; Mitsunaga , T. ; Kato , T. ; Kinoshita , T. ; Kita , Y. ; Kusunoki , T. ; Terai , T. ; Yoshida , K. ; Shiokawa , Y. Discovery of 6-oxo-3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-1(6H)-pyridazinebutanoic acid (FK 838): A novel non-xanthine adenosine A1 receptor antagonist with potent diuretic activity . J. Med. Chem. 1999 , 42 , 779 – 783 .
   PubMed Web of Science ®Google Scholar
• Cignarella , G. ; Loriga , M. ; Pinna , G. A. ; Pirisi , M. A. ; Schiatti , P. ; Selva , D. Unexpected anti-inflammatory activity of rigid structures derived from antihypertensive 6-arylpyridazinones, III: Synthesis and activity of 7-fluoro- and 5-keto-5H-indeno(1,2-c)pyridozines . Farmaco Ed. Sci. 1982 , 37 , 133 – 144 .
   PubMedGoogle Scholar
• Sircar , I. ; Duell , B. L. ; Cain , M. H. ; Burke , S. E. ; Bristol , J. A. Cardiotonic agents, 4: Synthesis and biological evaluation of N-substituted 2,4,4a,5-tetrahydro-3H-indeno[1,2-c]pyridazin-3-ones: Rigid structures derived from CI-930 and analogs . J. Med. Chem. 1986 , 29 , 2142 – 2148 .
   PubMed Web of Science ®Google Scholar
• Barlocco , D. ; Cignarella , G. ; Piaz , V. D. ; Giovannoni , M. P. ; De Benedetti , P. G. ; Fanelli , F. ; Montesano , F. ; Poggesi , E. ; Leonardi , A. Phenylpiperazinylalkylamino substituted pyridazinones as potent α 1 adrenoceptor antagonists . J. Med. Chem. 2001 , 44 , 2403 – 2410 .
   PubMed Web of Science ®Google Scholar
• BASF website: www.basf.com
   Google Scholar
• Nara , S. ; Martinez , J. ; Wermuth , C. G. ; Parrot , I. Palladium-catalysed cross-coupling reactions on pyridazine moieties . Synlett 2006 , 3185 – 3204 .
   Google Scholar
• Salives , R. ; Dupas , G. ; Ple , N. ; Queguiner , G. ; George , A. T. P. ; Sevrin , M. ; Frost , J. ; Almario , A. ; Li , A. Solid-phase syntheses of 6-arylpyridazin-3(2H)-ones. J. Comb. Chem. 2005, 7, 414–420.
   PubMedGoogle Scholar
• (a) Mederski , W. W. K. R. ; Lefort , M. ; Germann , M. ; Kux , D. N-Aryl heterocycles via coupling reactions with arylboronic acids . Tetrahedron 1999 , 55 , 12757 – 12770 ; (b) Coelho , A. ; Sotelo , E. ; Novoa , H. ; Peeters , O. M. ; Blaton , N. ; Ravina , E. Pyridazine derivatives, part 39: Reactivity of 5-iodopyridazin-3(2H)-ones in palladium-catalysed reactions . Tetrahedron 2004 , 60 , 12177 – 12189 ; (c) Cao , P. ; Qu , J. ; Burton , G. ; Rivero , R. A. Facile synthesis of 6-aryl 5-N-substituted pyridazinones: Microwave-assisted Suzuki−Miyaura cross coupling of 6-chloropyridazinones . J. Org. Chem. 2008 , 73 , 7204 – 7208 ; (d) Maes , B. U. W. ; R'kyek , O. ; Kosmrlj , J. ; Lamiere , G. L. F. ; Esmans , E. ; Rozenski , J. ; Dommisse , R. A. ; Haemers , A. Suzuki reactions on chloropyridazinones: An easy approach towards arylated 3(2H)-pyridazinones . Tetrahedron 2001 , 57 , 1323 – 1330 ; (e) Crespo , A. ; Meyers , C. ; Coelho , A. ; Yanez , M. ; Fraiz , N. ; Sotelo , E. ; Maes , B. U. W. ; Laguna , R. ; Cano , E. ; Lemiere , G. L. F. ; Ravina , E. Pyridazines, part 41: Synthesis, antiplatelet activity, and SAR of 2,4,6-substituted 5-(3-oxo-3-phenylprop-1-en-1-yl)- or 5-(3-phenylprop-2-enoyl)pyridazin-3(2H)-ones . Bioorg. Med. Chem. Lett. 2006 , 16 , 1080 – 1083 ; (f) Gong , Y. ; Barbay , J. K. ; Kimball , E. S. ; Santulli , R. J. ; Fisher , M. C. ; Dyatkin , A. B. ; Miskowski , T. A. ; Hornby , P. J. ; He , W. Synthesis and SAR of pyridazinone-substituted phenylalanine amide α 4 integrin antagonists . Bioorg. Med. Chem. Lett. 2008 , 18 , 1331 – 1335 ; (g) Clapham , K. M. ; Batsanov , A. S. ; Greenwood , R. D. R. ; Bryce , M. R. ; Smith , A. E. ; Tarbit , B. Functionalized heteroarylpyridazines and pyridazin-3(2H)-one derivatives via palladium-catalyzed cross-coupling methodology . J. Org. Chem. 2008 , 73 , 2176 – 2181 .
   Web of Science ®Google Scholar
• Ghate , M. D. ; Jadhav , V. B. ; Shastri , L. A. ; Kulkarni , M. V. ; Kulkarni , G. M. ; Chen , C. H. ; Sun , C. M. 5-Phenylpyridazinones—A serendipitous route from coumarins . Tetrahedron Lett. 2008 , 49 , 4394 – 4396 .
   Web of Science ®Google Scholar
• Kulkarni , M. V. ; Patil , V. D. Studies on coumarins, I . Arch. Pharm. 1981 , 314 , 708 – 711 .
   PubMed Web of Science ®Google Scholar
• Burger , A. ; Ullyot , G. E. Analgesic studies: β-Ethyl and β-isopropylamine derivatives of pyridine and thiazole . J. Org. Chem. 1947 , 12 , 342 – 355 .
   PubMed Web of Science ®Google Scholar
• Mustafa , A. ; Hishmat , O. H. ; Wassef , M. E. Reaktionen substituierter Cumarine, Furocumarine und Khellinon-styryl-Derivate mit Hydrazin und Phenylhydrazin . Ann. Chem. 1966 , 692 , 166 – 173 .
   Google Scholar
• (a) Takagi , K. ; Morita , H. ; Nagahara , K. ; Takada , A. Sur les possibilites de formation de pyrimidines a partir de la dibromo-3,4 dihydro-3,4 coumarine . Chem. Pharm. Bull. 1982 , 30 , 4526 – 4528 ; (b) Morita , H. ; Tanaka , M. ; Takagi , K. Synthesis and some reactions of 6-(2-hydroxyphenyl)-2-thiouracils . Chem. Pharm. Bull. 1983 , 31 , 3728 – 3731 .
   Google Scholar
• Sosnovskikh , Y. V. ; Boris , I. U. ; Ivan , I. V. Unusual reaction of 2-(trifluoromethyl)-1,2-dihydro-3λ6-thieno-[2,3-c]chromen-3,3,4-triones with hydrazine as a new route to 3-hydrazinopyridazine derivative s. J. Org. Chem. 2002 , 67 , 6738 – 6742 .
   PubMed Web of Science ®Google Scholar