350994-49-9Relevant articles and documents
Revisiting the reaction of β-chloroacroleins with 2-aminophenol: a new observation
Bera, Rabin,Dhananjaya,Singh, Shambu Nath,Ramu,Kiran, Sai Uday,Kumar, P. Rajender,Mukkanti,Pal, Manojit
, p. 582 - 589 (2008)
The reaction of β-chloroacrolein with 1 equiv of 2-aminophenol in DMF proceeds smoothly to afford 11-hydroxy derivative of chromenoquinoline in good yield. This single pot method allows for a rapid access to a variety of chromenoquinolines or oxepinoquinolines depending on the nature of β-chloroacrolein used. The structures were established by spectroscopic data and further confirmed by X-ray diffraction analysis. A plausible mechanism for this reaction has been proposed. The reaction seemed to proceed via a chloroimine species, whose intermediacy has been established, followed by the construction of the fused quinoline ring.