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

Autor:	J. S. Mahanty, P. Das, Nitya G. Kundu, M. De
Rok vydání:	1997
Předmět:	Chemistry Yield (chemistry) Organic Chemistry Drug Discovery Synthon chemistry.chemical_element Biochemistry Medicinal chemistry Catalysis Palladium
Zdroj:	Tetrahedron. 53:13397-13418
ISSN:	0040-4020
DOI:	10.1016/s0040-4020(97)00852-1
Popis:	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 .
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::de9e7e1fd1f9a136bad924ddfdaa60c5 https://doi.org/10.1016/s0040-4020(97)00852-1 Zobrazit plný text záznamu Full Text from ScienceDirect