PALLADIUM-CATALYZED HETEROANNULATION WITH ACETYLENIC CARBINOLS AS SYNTHONS - SYNTHESIS OF QUINOLINES AND 2,3-DIHYDRO-4(1H)-QUINOLONES

Authors
MAHANTY JS DE M DAS P KUNDU NG
Citation
Js. Mahanty et al., PALLADIUM-CATALYZED HETEROANNULATION WITH ACETYLENIC CARBINOLS AS SYNTHONS - SYNTHESIS OF QUINOLINES AND 2,3-DIHYDRO-4(1H)-QUINOLONES, Tetrahedron, 53(39), 1997, pp. 13397-13418
Citations number
80
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
39
Year of publication
1997
Pages
13397 - 13418
Database
ISI
SICI code
0040-4020(1997)53:39<13397:PHWACA>2.0.ZU;2-1
Abstract
omicron-Iodoanilides 4 reacted with terminal acetylenic carbinols 5 un der palladium-catalyzed conditions to yield omicron-substituted anilid es 6. Most of the anilides 6 could be cyclized with NaOEt/EtOH to 2-ar ylquinolines 2. omicron-Iodoanilines 7 reacted with carbinols 5 leadin g to 8 which on palladium(II) assisted cyclisation afforded substitute d quinolines 2. An excellent synthesis of the alkaloid dubamine (2n) i s reported. Also, the anilides 6 on acid-catalyzed rearrangement, depr otection and cyclisation led to the 2-aryl-2,3-dihydro-4(1H)-quinolone s 16. (C) 1997 Elsevier Science Ltd.