131534-33-3Relevant academic research and scientific papers
THE SYNTHESIS AND CHEMISTRY OF AZOLENINES. PART 20 ISOLATION OF 3H-PYRROLE-5-CARBOXYLATE ESTERS AND FRAGMENTATION PRODUCTS FROM THE REACTION BETWEEN 2,2-DISUBSTITUTED 1,3-DIKETONES AND GLYCINE ETHYL ESTER HYDROCHLORIDE
Lee, Sze-Ming,Sammes, Michael P.
, p. 2401 - 2410 (2007/10/02)
The reaction between 3,3-dimethylpentane-2,4-dione (12a) and glycine ethyl ester hydrochloride (13) in the presence of sodium acetate and acetic acid gives moderate amounts each of ethyl 2,3,3,4-tetramethyl-3H-pyrrole-5-carboxylate (17a), a hydroxypyrroline precursor (15a) and a fragmentation product ethyl acetamidoacetate (14a).With the more sterically-crowded 2,2-dimethyl-1-phenylbutane-1,3-dione (12b), only very small amounts of two regioisomeric 3H-pyrroles (17b) and (18b) are found, fragmentation being the major reaction pathway: other 2,2-disubstituted 1,3-diketones studied gave only fragmentation products.A reaction scheme accounting for the various products is proposed.
