Facile Oxidation of Fused 1,4-Dimethoxybenzenes to 1,4-Quinones Using NBS: Fine-Tuned Control over Bromination and Oxidation Reactions
摘要:
[GRAPHICS]Fused 1,4-dimethoxybenzenes could be oxidized to benzoquinones by either direct oxidation or demethylation-oxidation. The oxidative demethylation of 5,8-dimethoxy-2-methylquinoline using 1.1 equiv of NBS in aqueous THF and a catalytic amount of H2SO4 at 20 degreesC for 5 min gave 2-methylquinoline-5,8-dione in 98% yield without bromination. Moreover, we can control either bromination or oxidative demethylation, or both reactions.
Simple preparation of 7-alkylamino-2-methylquinoline-5,8-diones: regiochemistry in nucleophilic substitution reactions of the 6- or 7-bromo-2-methylquinoline-5,8-dione with amines
作者:Han Young Choi、Dae Yoon Chi
DOI:10.1016/j.tet.2004.04.041
日期:2004.5
7-Alkylamino-2-methylquinoline-5,8-diones (7) were prepared from 6-bromo-2-methylquinoline-5,8-dione (2) not from 7-bromo-2-methylquinoline-5,8-dione (1). The chemistry of the transformation of 6-bromo-2-methylquinoline-5,8-dione (2) and various alkylamines, such as piperidine, 2-methylaziridine, benzylamine, n-butylamine, cyclohexylamine, t-butylamine, and ammonia, to 7-alkylamino compounds 7 as well
This invention relates to a class of quinoline quinones, which are useful for the therapy of immediate hypersensitivity reactions, such as asthma, and in treating any condition characterized by excessive release of leukotrienes. This invention also includes a method for treating these conditions, which comprises administering to animals, including humans, an effective dose of the quinoline quinone compounds. A further part of this invention is pharmaceutical formulations containing these pharmacologically-active compounds.
The ability of 2-ethoxybut-2-enal N,N-dimethylhydrazone to give with quinoline 5,8-diones or 1,4-naphtho-quinones, either a [4+2] cycloaddition in a neutral medium or a [3+2] process in the presence of trifluoroacetic acid is described. A 2D 1H-13C HMBC and 1D 1H NOE DIFF study is made in order to confirm the structures.
2-乙氧基丁-2-烯醛N,N-二甲基hydr与喹啉5,8-二酮或1,4-萘醌生成中性介质中[4 + 2]环加成或[3+]的能力[2]描述了在三氟乙酸存在下的方法。为了确定结构,进行了2D 1 H- 13 C HMBC和1D 1 H NOE DIFF研究。
The invention relates to compounds of formula (I) or formula (II) which have anti-inflammatory activity and comprise a new class of NSAIDs. The compounds are therefore useful for treating inflammatory diseases or disorders. The invention also relates to pharmaceutical compositions containing these compounds, as well as methods of treating inflammatory diseases or disorders using compounds of formula (III) or formula (IV).