53074-96-7Relevant articles and documents
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Ungnade,Kissinger
, p. 666 (1959)
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Direct C?H Carbamoylation of Nitrogen-Containing Heterocycles
Jouffroy, Matthieu,Kong, Jongrock
supporting information, p. 2217 - 2221 (2019/01/30)
Nucleophilic radical additions at innately electrophilic C(sp2) centers are perfectly suited for the direct functionalization of heterocycles. Using bench stable and commercially available alkyl oxamate and oxamic acid derivatives in combination with photoredox catalysis, a direct carbamoylation of heterocycles yielding amide functionalized pharmacophores in a single step is reported. The reaction conditions reported are compatible with structurally complex heterocyclic substrates of pharmaceutical interest. Notably, derivatives containing functional groups incompatible with standard amidation reactions, such as carboxylic acids and unprotected amines, were found to be amenable to this reaction paradigm.
Metal-, Photocatalyst-, and Light-Free Direct C-H Acylation and Carbamoylation of Heterocycles
Westwood, Matthew T.,Lamb, Claire J. C.,Sutherland, Daniel R.,Lee, Ai-Lan
supporting information, p. 7119 - 7123 (2019/09/03)
Direct C-H acylations and carbamoylations of heterocycles can now be readily achieved without requiring any conventional metal, photocatalyst, electrocatalysis, or light activation, thus significantly improving on sustainability, costs, toxicity, waste, and simplicity of the operational procedure. These mild conditions are also suitable for gram-scale reactions and late-stage functionalizations of complex molecules, including pharmaceuticals, N,N-ligands, and light-sensitive molecules.
