59762-03-7Relevant academic research and scientific papers
Direct transformation of Baylis-Hillman acetates into N-substituted quinolones through an SN2′→ SNAr→(Δ3,4-Δ2,3 shift)→oxidation sequence
Napoleon, John Victor,Kannoth Manheri, Muraleedharan
, p. 3379 - 3388 (2011)
When subjected to tandem SN2-SNAr cyclization in the presence of alkyl or aralkyl amines, Baylis-Hillman acetates gave the corresponding 1,2-dihydroquinolines, which on simple exposure to light and oxygen afforded the corresponding 4- and 2-quinolones through sensitized oxidation or a 3,4-2,3 shift oxidation cascade. The mechanism of the oxidation step, the stabilities of the 1,2- and 1,4-dihydroquinolines in solution and in the solid state, and the synthetic elaboration of the key intermediates to known therapeutic agents are discussed. Georg Thieme Verlag Stuttgart · New York.
