Tetrahedron

Palladium-catalyzed heteroannulation with acetylenic carbinols as synthons-synthesis of quinolines and 2, 3-dihydro-4 (1H)-quinolones

JS Mahanty, M De, P Das, NG Kundu

Index: Mahanty, Jyan S.; De, Mahuya; Das, Palas; Kundu, Nitya G. Tetrahedron, 1997 , vol. 53, # 39 p. 13397 - 13418

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Citation Number: 69

Abstract

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 ...

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