Thermal rearrangement of O-(2-pyridyl)oximes

Abstract

The experiment was repeated using the procedure outlined (19) R. C. Weast, Ed., "Handbook of Chemistry and Physics," 49th ed, Chemical Rubber Publishing Co., Cleveland, Ohio, 1968, p C520. above except the reactants were refluxed in 100 ml of ethanol to give 1.80 g (35%) of 4 and 5.3 g of crude 9.

Rearrangement of N-Oxyenamines and Related Reactions

“…75 This process becomes dominant for formation of the 2-pyridone derivatives 97. 82 Milder reaction conditions (HCl in acetic acid at 20−25 °C) allows in some cases isolation of the imine salts 94. 67,83 Side processes arising from the initial oxime ether 93 undergoing hydrolysis 84 or other migrations 75 have also been reported.…”

The Elusive Paal–Knorr Intermediates in the Trofimov Synthesis of Pyrroles: Experimental and Theoretical Studies

“…In 1970 Sheradsky demonstrated that the O -vinyl oxime derived from the addition of acetophenone oxime to dimethylacetylene dicarboxylate can be thermally rearranged to the corresponding pyrrole. , This synthetic approach was further developed by Trofimov who showed that variously substituted pyrroles could be obtained from ketoximes and unactivated alkynes under superbasic conditions . Although the Trofimov reaction is limited by the harsh reaction conditions, the lack of regioselectivity and poor performance observed for substituted alkynes, it has been successfully applied in a number of pyrrole syntheses. , Recently, Camp and co-workers have developed procedures that provide access to pyrroles with EWG-groups, that are not accessible under classical Trofimov reaction conditions, via nucleophilic catalysis and gold-multifaceted catalysis approach. − …”