Synthesis of 2H-1,4-Oxazin-3(4H)-One Utilizing Umpolung Reaction to α-Hydrazonoketone

被引:0
|
作者
Mizota, Isao [1 ]
Oshima, Keiji [1 ]
Hoshiai, Nozomi [1 ]
Yamamoto, Ayaki [1 ]
Mitani, Masaki [1 ]
Batool, Rabbia [2 ]
Liu, Bo-Tau [3 ]
Shimizu, Makoto [1 ,4 ,5 ]
机构
[1] Mie Univ, Grad Sch Engn, Dept Appl Chem, Tsu, Mie 5148507, Japan
[2] Univ Gujrat, Fac Sci, Dept Zool, Gujrat 50700, Punjab, Pakistan
[3] Natl Yunlin Univ Sci & Technol, Dept Chem & Mat Engn, Yunlin 64002, Taiwan
[4] Nanjing Tech Univ, Sch Energy Sci, Nanjing 211816, Jiangsu, Peoples R China
[5] Nanjing Tech Univ, Engn Coll, Nanjing 211816, Jiangsu, Peoples R China
基金
日本学术振兴会;
关键词
Cyclization; <italic>N</italic>-Methylation; Nucleophilic Addition; 1,4-Oxazine; Umpolung; N-ALKYLATION; IMINO ESTERS; 1,4-BENZOXAZINE DERIVATIVES; IMINOESTERS; CYCLIZATION; APREPITANT; ALLYLATION; ADDITIONS; REAGENTS; ACIDS;
D O I
10.1002/ajoc.202400698
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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 alpha-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 alpha-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.
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页数:5
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