基于氨甲酰基硅烷的β-硝基酰胺衍生物的合成
收稿日期: 2022-06-14
修回日期: 2022-07-01
网络出版日期: 2022-07-21
基金资助
山西省留学回国人员基金(0713); 山西省自然科学基金(2012011046-9); 山西省1331工程和山西师范大学有机化学优质课程(2019YZKC-13)
Synthesis of β-Nitroamide Derivatives Based on Carbamoylsilane
Received date: 2022-06-14
Revised date: 2022-07-01
Online published: 2022-07-21
Supported by
Shanxi Provincial Foundation for Returnees Overseas Scientists(0713); Natural Science Foundation of Shanxi Province(2012011046-9); 1331 Engineering of Shanxi Province and the Organic Chemistry Quality Course of Shanxi Normal University(2019YZKC-13)
用氨甲酰基硅烷作氨甲酰基源, 对α-硝基-2-烯酸乙酯进行直接氨酰基化反应, 在不加催化剂温和条件下, 可以53%~96%的分离收率得到β-硝基酰胺衍生物. 此方法底物(或官能团)适用范围广, 在双键上可连接脂肪烃基、芳香烃基、杂芳香烃基和不饱和芳香烃基. 通过不同结构的氨甲酰基硅烷的选择, 此方法可合成β-硝基叔酰胺和甲氧甲基保护的仲酰胺衍生物. 该合成方法具有反应条件温和、产物收率较高、副产物较少、立体选择性较强以及后处理容易等优点, 既是一种制备β-硝基酰胺衍生物的新方法, 也是进一步合成具有潜在应用价值的β-氨基酰胺的新方法.
李俊飞 , 韩宇玲 , 刘艳红 , 陈建新 . 基于氨甲酰基硅烷的β-硝基酰胺衍生物的合成[J]. 有机化学, 2022 , 42(11) : 3880 -3889 . DOI: 10.6023/cjoc202206014
Using carbamoylsilane as an carbamoyl source, the direct aminocarbonylation of α-nitro-2-enoic acid ethyl ester afforded β-nitroamide derivatives in 53%~96% separation yields under mild conditions without use of catalysts. The protocol has a wide range of substrates (or functional groups), tolerated a nitroalkenes bearing different groups on the C=C bond such as aliphatic group, aryl, hetero aryl and unsaturated aryl. This procedure allows the preparation of various β-nitroamides including β-nitro tertiary amide derivatives and methoxymethyl-protecting β-nitro secondary amide derivatives by the selection of various carbamoylsilanes. The synthesis method has the advantages of mild reaction conditions, good to excellent yields, less by-products, strong stereoselectivity and easy post-processing. It is a new method for preparing β-nitroamide derivatives and then synthesizing β-aminoamides with potential application value.
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