Pyridazine derivatives. Part 38: Efficient Heck alkenylation at position 5 of the 6-phenyl-3(2H)-pyridazinone system

Tetrahedron Letters

Volumn 45, Issue 17, 2004, Pages 3459-3463

  Coelho, Alberto ^a   Sotelo, Eddy ^a   Novoa, Héctor ^b   Peeters, Oswald M ^b   Blaton, Norbert ^b   Raviña, Enrique ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^b UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

Heck coupling; Phthalazinones; Pyridazinones

Indexed keywords

6 PHENYL 3(2H) PYRIDAZINONE; ALKENYL GROUP; ANTITHROMBOCYTIC AGENT; LIGAND; PALLADIUM; PHOSPHINE DERIVATIVE; PYRIDAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CROSS COUPLING REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; HECK REACTION;

EID: 1842637310     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.03.005     Document Type: Article

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32. 2 (0.10 mmol) and triethylamine (1.52 mmol) in DMF (10 mL) was flushed with argon for 5 min and then deoxygenated and purged. The mixture was stirred and heated under reflux (oil bath 120°C) under argon until the starting material had been consumed. The reaction mixture was cooled, filtered through a Celite pad and the resulting solution was concentrated to dryness under reduced pressure. The residue was purified by column chromatography on silica gel (AcOEt/hexane, 1:2).
33. +] 350.0266, found 350.0270.
34. +] 370.1529, found 370.1532.
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39. 2 (0.10 mmol) and triethylamine (1.52 mmol) in DMF (10 mL) was flushed with argon for 5 min and then deoxygenated and purged. The mixture was stirred and heated under reflux (oil bath 120°C) under argon until the starting material had been consumed. The reaction mixture was cooled, filtered through a Celite pad and the resulting solution was concentrated to dryness under reduced pressure. The residue was purified by column chromatography on silica gel (AcOEt/hexane, 1:2).
40. 4 requires C: 67.44; H: 5.36, N: 8.28, Found: C: 67.45; H: 5.39; N: 8.25.
41. Coelho, A.; Sotelo, E.; Novoa, H.; Peeters, M. O.; Blaton, N.; Raviña, E., to be published.
42. 2 (0.10 mmol) and triethylamine (1.52 mmol) in DMF (10 mL) was flushed with argon for 5 min and then deoxygenated and purged. The mixture was stirred and heated under reflux (oil bath 120°C) under argon until the starting material had been consumed. The reaction mixture was cooled, filtered through a Celite pad and the resulting solution was concentrated to dryness under reduced pressure. The residue was purified by column chromatography on silica gel (AcOEt/hexane, 1:2).
43. 6 300 MHz): 165.9, 160.5, 146.4, 139.9, 139.1, 134.4, 129.8, 129.3, 129.0, 127.5, 125.7, 125.4, 81.9, 58.3, 52.5.
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45. 3 requires C: 65.62; H: 4.72; N: 10.93, Found: C: 65.70; H: 4.70; N: 10.93.