128260-01-5Relevant academic research and scientific papers
THE SYNTHESIS AND CHEMISTRY OF AZOLENINES. PART 21. REVERSIBLE INTERCONVERSIONS OF ISOMERIC 2H- AND 3H-PYRROLES DURING THERMAL REARRANGEMENT INTO 2,3-DIMETHYL-4,5-DIPHENYL-1H-PYRROLE
Cheung, William M. L.,Sammes, Michael P.
, p. 2348 - 2355 (2007/10/02)
Thermal rearrangments of 2,3-dimethyl-2,5-diphenyl-2H-pyrrole 1 and 2,3-dimethyl-3,5-diphenyl-3H-pyrrole 3 at 270 deg C for 12 h yield the same product 2,3-dimethyl-4,5-diphenyl-1H-pyrrole 5.On heating either 1 or 3 for only 1 h, four isomeric 2H- and 3H-pyrroles are observed, demonstrating the facile interconversion of these compounds prior to non-reversible rearrangment into the 1H-pyrrole 5.No traces of other 1H-pyrrole isomers were detected.
Synthesis and Chemistry of Azolenines. Part 16. Preparation of both 3H- and 2H-Pyrroles from 2,2-Disubstituted 1,4-Diketones via the Paal-Knorr Reaction, and Isolation of Intermediate 2-Hydroxy-3,4-dihydro-2H-pyrroles
Lui, Kon-Hung,Sammes, Michael P.
, p. 457 - 468 (2007/10/02)
Treatment of 2,2-disubstituted 1,4-diketones (1) with liquid ammonia gives high yields of isolable isomeric 2-hydroxy-3,4-dihydro-2H-pyrroles (10) and (11), many of which may be dehydrated to 3H-pyrroles (2) together, in certain cases, with isomeric methylene-pyrrolines (14) and (15).When heated in acetic acid with ammonium acetate, the diketones (1) yield 2H-pyrroles (18), sometimes in admixture with 3H-pyrroles (2) from which they are formed by rearrangement.The diketones (1), including some novel examples, are prepared from nitro-ketones (6) by the Nef reaction, as well as other methods.
