Journal
TETRAHEDRON
Volume 58, Issue 48, Pages 9713-9721Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(02)01285-1
Keywords
palladium; Suzuki reaction; pyridazinones; hydrolysis; coumarins
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Easily accessible 2-substituted 4-aryl-5-methoxy- and 2-substituted 5-aryl-4-methoxypyridazin-3(2H)-ones were transformed into the corresponding aryl-hydroxypyridazin-3(2H)-ones by alkaline hydrolysis. The use of these compounds in the synthesis of 2-substituted 4,5-diarylpyridazin-3(2H)-ones with two differently substituted aryl groups was investigated. Two aryl-hydroxypyridazin3(2H)-ones, 2-(2-benzyl-5-hydroxy-3-oxo-2,3-dihydropyridazin-4-yl)benzaldehyde and 2-(1-benzyl-5-hydroxy-6-oxo-1,6-dihydropyridazin-4-yl)benzaldehyde, were transformed into 2-benzyl-1H-isochromeno[3,4-d]pyridazine-1,6(2H)-dione and 3-benzyl-3H-isochromeno[3,4-d]pyridazine-4,6-dione, respectively, via oxidation of the formyl group with KMnO4 followed by lactonization. (C) 2002 Elsevier Science Ltd. All rights reserved.
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