148564-90-3Relevant academic research and scientific papers
2-Alkylindoles via palladium-catalyzed reductive cyclization of ethyl 3-(o-trifluoroacetamidophenyl)-1-propargyl carbonates
Ambrogio, Ilaria,Cacchi, Sandro,Fabrizi, Giancarlo
, p. 7721 - 7725 (2007)
The reaction of ethyl 3-(o-trifluoroacetamidophenyl)-1-propargyl carbonates with formate anions in the presence of Pd(PPh3)4 affords 2-alkylindoles in good to excellent yields.
Synthesis of free NH 2-(aminomethyl)indoles through copper-catalyzed reaction of 3-(ortho-trifluoroacetamidophenyl)-1-propargylic alcohols with amines and palladium/copper- cocatalyzed domino three-component Sonogashira cross-coupling/cyclization/substitu
Cacchi, Sandro,Fabrizi, Giancarlo,Iazzetti, Antonia,Molinaro, Carmela,Verdiglione, Rosanna,Goggiamani, Antonella
supporting information, p. 1053 - 1059 (2015/03/30)
Free NH 2-(aminomethyl)indoles have been prepared via copper-catalyzed cyclization of 3-(ortho-trifluoroacetamidophenyl)-1-propargylic alcohols in the presence of primary or secondary amines. The synthesis has been developed into a simple and very efficie
Sequential alkylation/cyclization/isomerization of ethyl 3-(o-trifluoroacetamidoaryl)-1-propargylic esters: A new route to 2-acyl- and 2-ethoxycarbonyl-3-alkenyl indoles
Ambrogio, Ilaria,Arcadi, Antonio,Cacchi, Sandro,Fabrizi, Giancarlo,Goggiamani, Antonella,Marinelli, Fabio
, p. 9494 - 9498 (2013/10/08)
The reaction of ethyl 3-(o-trifluoroacetamidoaryl)-1-propargylic esters with ethyl iodoacetate or α-bromoacetophenone in the presence of K 2CO3 in DMSO provides a new simple access to 2-acyl- and 2-ethoxycarbonyl-3-alkenyl indoles.
3-(o-Trifluoroacetamidoaryl)-1-propargylic esters: common intermediates for the palladium-catalyzed synthesis of 2-aminomethyl-, 2-vinylic, and 2-alkylindoles
Ambrogio, Ilaria,Cacchi, Sandro,Fabrizi, Giancarlo,Prastaro, Alessandro
experimental part, p. 8916 - 8929 (2009/12/07)
3-(o-Trifluoroacetamidoaryl)-1-propargylic esters have been used as common synthetic intermediates for the preparation of a variety of 3-unsubstituted 2-substituted indoles. Treating ethyl 3-(o-trifluoroacetamidoaryl)-1-propargylic carbonates unsubstituted or containing an aryl substituent at the propargylic carbon with piperazines and Pd(PPh3)4 in THF at 80 °C affords 2-(piperazin-1-ylmethyl)indoles in excellent yields. Good to excellent yields of 2-aminomethylindoles are also obtained with other secondary amines. Ethyl 3-(o-trifluoroacetamidoaryl)-1-propargylic carbonates bearing an alkyl substituent at the propargylic carbon and ethyl 3-(o-trifluoroacetamidoaryl)-1-propargylic acetates disubstituted at the propargylic carbon give 2-vinylic indoles with the Pd(OAc)2/PPh3 combination and Et3N in THF at 80 °C. Formation of 2-vinylic indoles is quite stereoselective, generating trans vinylic derivatives, at least with the substrates that we have investigated. In the presence of formic acid, Et3N, and Pd(PPh3)4 in MeCN at 80 °C, ethyl 3-(o-trifluoroacetamidoaryl)-1-propargylic carbonates afford 2-alkylindoles in good to excellent yields.
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.
Synthesis of Quinolines and 2,3-Dihydro-4(1H)-quinolones. Palladium Catalysed Reaction of o-Iodoanilides with Acetylenic Carbinols
Kundu, Nitya G.,Mahanty, Jyan S.,Das, Palas,Das, Biswajit
, p. 1625 - 1628 (2007/10/02)
A facile and general synthesis of quinolines and 2,3-dihydro-4(1H)-quinolones was accomplished through palladium catalysed reaction of o-iodoanilides with acetylenic carbinols.Key Words: quinolines; 2,3-dihydro-4(1H)-quinolones; palladium catalysis; o-iodoanilines; acetylenic carbinols.
