4-乙酰氧基丙二烯酸酯的1,3-偶极环加成反应：通往2,3-二氢吡唑、2,3-二氢异恶唑和中氮茚的途径。
1,3-Dipolar Cycloadditions of 4-Acetoxy Allenoates: Access to 2,3-Dihydropyrazoles, 2,3-Dihydroisoxazoles, and Indolizines.
作者信息
Li Falin, Chen Jiangfei, Hou Yading, Li Yujie, Wu Xin-Yan, Tong Xiaofeng
机构信息
Shanghai Key Laboratory of Functional Materials Chemistry, East China University of Science and Technology , 130 Meilong Road, Shanghai 200237, China.
Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University , 1 Gehu Road, Changzhou 213164, China.
出版信息
Org Lett. 2015 Nov 6;17(21):5376-9. doi: 10.1021/acs.orglett.5b02724. Epub 2015 Oct 15.
The thermal 1,3-dipolar cycloadditions of 4-acetoxyallenoates 1 with various dipoles have been reported. When azomethine imines and nitrones are used as the 1,3-dipole partner, the corresponding reactions afford 2,3-dihydropyrazole and 2,3-dihydroisoxazole derivatives, respectively. These reactions might proceed via a thermal 1,3-dipolar cycloaddition and the subsequent elimination of HOAc. In addition, allenoates 1 react well with in situ generated azomethine ylides in which a similar cycloaddition pathway is followed by oxidative aromatization to give indolizine derivatives.
4-乙酰氧基联烯酸酯1与各种偶极体的热1,3-偶极环加成反应已有报道。当甲亚胺亚胺和硝酮用作1,3-偶极体反应物时，相应的反应分别得到2,3-二氢吡唑和2,3-二氢异恶唑衍生物。这些反应可能通过热1,3-偶极环加成反应以及随后乙酸的消除来进行。此外，联烯酸酯1与原位生成的甲亚胺叶立德反应良好，其中类似的环加成途径之后是氧化芳构化反应，生成中氮茚衍生物。
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