Dr. Isao Mizota, Keiji Oshima, Nozomi Hoshiai, Ayaki Yamamoto, Masaki Mitani, Rabbia Batool, Prof. Dr. Bo-Tau Liu, Prof. Dr. Makoto Shimizu
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引用次数: 0
摘要
已知2h -1,4-恶氮辛-3(4H)- 1衍生物具有广泛的生物活性,如抗真菌,抗癌,受体拮抗剂和钾通道调节剂。α-腙酮是Umpolung反应的合适底物,是合成2h -1,4-恶嗪-3(4H)-Ones的理想底物。值得注意的是,α-腙酮的Umpolung n -甲基化在温和和极短的反应时间内定量进行,这在常规反应中是难以实现的。此外,我们还开发了在氯乙酰氯存在下的串联Umpolung反应/还原/ n-酰基- o -烷基化反应,以高产得2h -1,4-恶嗪-3(4H)- 1。
Synthesis of 2H-1,4-Oxazin-3(4H)-One Utilizing Umpolung Reaction to α-Hydrazonoketone
2H-1,4-Oxazin-3(4H)-One Derivatives Are Known to Exhibit a Wide Range of Biological Activities Such as Antifungal, Anticancer, as Receptor Antagonists and Potassium Channel Modulators. In This Report, We Describe That α-Hydrazonoketone Is an Appropriate Substrate for the Umpolung Reaction and a Promising Candidate for the Synthesis of 2H-1,4-Oxazine-3(4H)-Ones. Notably, Umpolung N-Methylation for α-Hydrazonoketone Proceeded Quantitatively in a Mild and Extremely Short Reaction Time, Which Has Been Difficult to Achieve in the Conventional Reactions. Moreover, We Also Developed Tandem Umpolung Reaction/Reduction/N-Acyl-O-Alkylation to Afford 2H-1,4-Oxazin-3(4H)-Ones in High Yield in the Presence of Chloroacetyl Chloride.
期刊介绍:
Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC)
The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.