Selective electrophilic cyclization of <i>ortho</i>-carbonylarylacetylenols for the synthesis of cyclopenta[<i>a</i>]naphthalenol and 2-phenylnaphthalen-1-ol analogs
Selective cyclization occurred when the reaction was conducted in methyl trimethylacetate solvent which predominantly produced the 2-phenylnaphthalen-1-ol product through 6-endo-dig cyclization without elimination or the formation of cyclopenta[a]naphthalenol via shutting down the 5-exo-dig mode of cyclization. Switching the acid from a Brønsted acid to Bi(OTf)3 led to smooth reactions, providing
这项工作展示了一种通过选择性环化合成环戊[ a ]萘酚和2-苯基萘-1-醇类似物的新方法。采用邻炔基芳基烯酮作为常见底物,可以通过 2-卤代芳基苯乙酮和 pent-4-yn-1-ol 衍生物之间的 Sonogashira 偶联来制备。这些前体无需纯化即可通过在加热条件下用(+)-CSA处理来构建2-苯基萘-1-醇中间体。当反应在三甲基乙酸甲酯溶剂中进行时,发生选择性环化,该溶剂主要通过 6-内位环化产生 2-苯基萘-1-醇产物,而没有消除或通过关闭 5-外位环化形成环戊[ a ]萘酚。挖掘环化模式。将酸从布朗斯台德酸转换为 Bi(OTf) 3导致反应顺利,以中等至良好的产率提供环戊[ a ]萘酚产物。此外,我们还展示了利用2-苯基萘-1-醇制备萘醌,萘醌是生物活性和天然产物化合物的重要核心结构。
N4-PHENYL-QUINAZOLINE-4 -AMINE DERIVATIVES AND RELATED COMPOUNDS AS ERBB TYPE I RECEPTOR TYROSINE KINASE INHIBITORS FOR THE TREATMENT OF HYPERPROLIFERATIVE DISEASES