Base-Promoted, Metal- and Oxidant-Free C=C Bond Cleavage in Enaminones for Ambient Synthesis of NH2-Amidines

doi:10.6023/cjoc201912018

Abstract

The C=C double bond cleavage of NH₂-functionalized enaminones has been realized at room temperature to provide various N-sulfonyl amidines by reacting with sulfonyl azides. The reactions take place with good substrate tolerance in the presence of 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) without any metal or oxidant reagent. The ¹⁵N-labelling experiment on enaminone indicates that the sulfonyl azide component donates solely the sulfonamide fragment, and the reaction mechanism involving a key decomposition of the in situ generated 1,2,3-triazoline intermediate is convictively supported.

Key words: Enaminone, C=C bond cleavage, Metal-free, Oxidant-free, Amidines

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Wang Guodong, Guo Yanhui, Wan Jieping. Base-Promoted, Metal- and Oxidant-Free C=C Bond Cleavage in Enaminones for Ambient Synthesis of NH₂-Amidines[J]. Chinese Journal of Organic Chemistry, 2020, 40(3): 645-650.

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无金属和氧化剂温和条件下碱促进的烯胺酮碳-碳双键断裂合成NH₂-结构脒类化合物

Base-Promoted, Metal- and Oxidant-Free C=C Bond Cleavage in Enaminones for Ambient Synthesis of NH₂-Amidines

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无金属和氧化剂温和条件下碱促进的烯胺酮碳-碳双键断裂合成NH2-结构脒类化合物