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Synthesis of the dibenzo[f,h]phthalazine and dibenzo[f,h]cinnoline skeleton via a ‘Suzuki-Pd-catalyzed intramolecular arylation’ and a ‘Suzuki-Pschorr’ approach |
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| Authors: | Pál Tapolcsányi Bert UW Maes Katrien MonsieursGuy LF Lemière Zsuzsanna RiedlGyörgy Hajós Bart Van den DriesscheRoger A Dommisse Péter Mátyus |
| Institution: | a Department of Chemistry, University of Antwerp (RUCA), Groenenborgerlaan 171, B-2020 Antwerpen, Belgium b Department of Organic Chemistry, Semmelweis University, H?gyes E. u. 7., H-1092 Budapest, Hungary c Chemical Research Center, Institute of Chemistry, Hungarian Academy of Sciences, P.O. Box 17, H-1525 Budapest, Hungary |
| Abstract: | Palladium-catalyzed intramolecular arylation of 2-benzyl-5-(2-bromophenyl)-4-phenylpyridazin-3(2H)-one yielded hitherto unknown 2-benzyldibenzof,h]phthalazin-1(2H)-one. The synthesis of this new tetracyclic pyridazinone from 2-benzyl-5-(2-aminophenyl)-4-phenylpyridazin-3(2H)-one via a Pschorr type reaction was also investigated. Similarly, the construction of 2-methyldibenzof,h]cinnolin-3(2H)-one from 2-methyl-5-(2-bromophenyl)-6-phenylpyridazin-3(2H)-one and 2-methyl-5-(2-aminophenyl)-6-phenylpyridazin-3(2H)-one is also reported. Removal of the N-benzyl protective group of 2-benzyl-dibenzof,h]phthalazin-1(2H)-one with AlCl3 yielded unsubstituted dibenzof,h]phthalazin-1(2H)-one. |
| Keywords: | intramolecular arylation palladium Suzuki reaction Pschorr reaction pyridazinone |
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