134807-07-1Relevant academic research and scientific papers
Microwave-assisted synthesis of pyridylpyrroles from N-acylated amino acids
Harju, Kirsi,Manevski, Nenad,Yli-Kauhaluoma, Jari
, p. 9702 - 9706 (2009)
A small library of 3- and 4-pyridyl-substituted pyrroles was prepared from N-acylated amino acids. Nicotinoyl or isonicotinoyl chloride was used for the N-acylation of benzyl esters of amino acids. Debenzylation by palladium-catalyzed hydrogenation gave N-acylated amino acids. Dehydration of the acylated amino acids gave cyclic intermediates, münchnones or azlactones, which were treated in situ with alkynes in 1,3-dipolar cycloadditions. The starting materials were prepared in a parallel fashion, and microwave irradiation was used to facilitate the cycloaddition reactions. The regiochemistry of the cycloaddition was studied.
