- Copper-catalyzed aerobic dehydrogenation of C-C to C=C bonds in the synthesis of pyridazinones
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A simple and efficient procedure for the synthesis of pyridazin-3(2H)-ones through copper-catalyzed dehydrogenation of a single C-C bond of 4,5-dihydropyridazin-3(2H)-ones to a C=C bond with oxygen as the terminal oxidant is described. Functional groups including hydroxy, carboxylic, bromo, chloro, cyano, nitro and alkoxy were all tolerated under the reaction conditions. Moreover, this methodology was applied to the preparation of a series of structurally similar N-substituted 6-phenylpyridazinone compounds containing fluorine. The dehydrogenation reactions exhibit good yields and selectivity. Copper-catalyzed dehydrogenation of a C-C bond of 4,5-dihydropyridazinones to a C=C bond with oxygen as the terminal oxidant is described. Various functional groups were tolerated under the reaction conditions. The method was also applied to the preparation of a series of N-substituted 6-phenylpyridazinones containing fluoride. The dehydrogenation reactions exhibit good yields and selectivity.
- Liang, Lei,Yang, Guanyu,Xu, Fengrong,Niu, Yan,Sun, Qi,Xu, Ping
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supporting information
p. 6130 - 6136
(2013/09/24)
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- Pyridazine derivatives. XXIV. Efficient N-methylation of diversely substituted 3(2H)-pyridazinones using N,N-dimethylformamide dimethylacetal
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A series of diversely substituted 3(2H)-pyridazinones were efficiently N-methylated at position 2 by treatment with N,N-dimethylformamide dimethylacetal in DMF.
- Sotelo, Eddy,Ravina, Enrique
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p. 1675 - 1680
(2007/10/03)
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- ALKYLATION OF 6-OXO-1,6-DIHYDROPYRIDAZINES BY TRIETHYLOXONIUM FLUOROBORATE
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Irrespective of the nature of the substituents at positions 1 and 3 the heterocycle, 6-oxo-1-phenyl(methyl)-3-aryl-1,6-dihydropyridazines are alkylated by the action of triethyloxonium fluoroborate at the oxygen atom of the carbonyl group, forming heteroaromatic 1-ethoxypyridazinium salts.
- Volynets, N. F.,Smartseva, I. V.,Khramova, I. V.,Pavlova, L. A.
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p. 1604 - 1608
(2007/10/02)
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- Substituted 6-phenyl-3(2H)-pyridazinones useful as cardiotonic agents
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Substituted 6-phenyl-3(2H)-pyridazinone compounds are useful as cardiotonic agents. Said compounds cause a significant increase in myocardial contractility in the anesthetized dog. Said compounds are produced by reacting substituted γ-oxobenzenebutanoic acids with suitably substituted hydrazines to provide 6-phenyl-4,5-dihydro-3(2H)-pyridazinones which are dehydrogenated to the desired product. The intermediate 6-phenyl-4,5-dihydro-3(2H)-pyridazinones are themselves useful as cardiotonic agents.
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