Organic Letters
Organic Letters
5 years ago

Oxidative Trimerization of Amino Acids: Selective Synthesis of 2,3,5-Trisubstituted Pyridines

Oxidative Trimerization of Amino Acids: Selective Synthesis of 2,3,5-Trisubstituted Pyridines
An-Xin Wu, Jia-Chen Xiang, Yan Cheng, Zi-Xuan Wang, Yan-Dong Wu, Jin-Tian Ma, Miao Wang, Bo-Cheng Tang
An oxidative trimerization of three amino acids has been realized to furnish 2,3,5-trisubstuitued pyridines in both cross- and homo-trimerization types. This method is capable of converting simple linear biomass material to heterocycles, which features in the assembly of three amino acid branched chains into one aromatic ring. Molecular iodine triggers the sequential decarboxylation and deamination of amino acids and then promotes the selective formation of new C–N and C–C bonds.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01232

DOI: 10.1021/acs.orglett.7b01232

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