148564-93-6Relevant articles and documents
Palladium-catalyzed heteroannulation with acetylenic carbinols as synthons-synthesis of quinolines and 2,3-dihydro-4(1H)-quinolones
Mahanty, Jyan S.,De, Mahuya,Das, Palas,Kundu, Nitya G.
, p. 13397 - 13418 (2007/10/03)
o-Iodoanilides 4 reacted with terminal acetylenic carbinols 5 under palladium-catalyzed conditions to yield o-substituted anilides 6. Most of the anilides 6 could be cyclized with NaOEt/EtOH to 2-arylquinolines 2. o-Iodoanilines 7 reacted with carbinols 5 leading to 8 which on palladium(II) assisted cyclisation afforded substituted quinolines 2. An excellent synthesis of the alkaloid dubamine (2n) is reported. Also, the anilides 6 on acid-catalyzed rearrangement, deprotection and cyclisation led to the 2-aryl-2, 3-dihydro-4(1H)-quinolones 16.