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

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2025年 / 14卷 / 03期

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.

引用

页数：5

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