Synthesis of β-Nitroamide Derivatives Based on Carbamoylsilane

doi:10.6023/cjoc202206014

Abstract

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.

Key words: nucleophilic addition, carbamoylsilanes, β-nitroalkenes, aminocarbonylation, β-nitroamides

Cite this article

Junfei Li, Yuling Han, Yanhong Liu, Jianxin Chen. Synthesis of β-Nitroamide Derivatives Based on Carbamoylsilane[J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3880-3889.

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