23674-58-0Relevant academic research and scientific papers
Synthetic Route to Enaminones via Metal-Free Four-Component Sequential Reactions of Aryl Olefins with CHCl3, Et3N, and TBHP
Zhang, Jiantao,Zhou, Peng,Yin, Aiguo,Zhang, Shuhua,Liu, Weibing
, p. 8980 - 8986 (2021/06/30)
An efficient and modular strategy was used to obtain enaminones with a wide range of functional groupsviaa four-component sequential reaction. This reaction proceeded under mild conditions without a catalyst in one pot. Furthermore, the products could be transformed into thiadiazoles.
Alternative formation of amides and β-enaminones from aroyl chlorides using the TiCl4-trialkylamine reagent system
Leggio, Antonella,Comandè, Alessandra,Belsito, Emilia Lucia,Greco, Marianna,Lo Feudo, Lucia,Liguori, Angelo
, p. 5677 - 5683 (2018/08/17)
The TiCl4/NR3 reagent system has been successfully employed for the synthesis of amides and β-enaminones. The reaction of variously substituted benzoyl chlorides with the TiCl4/NR3 reagent system, by using two different experimental procedures (Method A and Method B), afforded alternatively the corresponding amides and β-enaminones as unique or major products. The two developed protocols were investigated with a series of tertiary amines. The reactions, modulated by the presence of TiCl4, provided the corresponding amides or β-enaminones with satisfactory yields. This paper reports a new method for carbon-carbon bond formation via the reaction of aroyl chlorides with the TiCl4/NR3 reagent system.
Silver-catalyzed efficient synthesis of enaminones from propargyl alcohols and amines
Li, Mengshun,Fang, Dongmei,Geng, Feng,Dai, Xianping
supporting information, p. 4747 - 4749 (2017/11/28)
Enaminones are used as the key intermediates to construct heterocyclic compounds with various bioactivities. In this study, a simple and efficient approach for the synthesis of enaminones via amination of propargyl alcohols was developed. Under the catalysis of Ag2CO3, the reaction proceeded smoothly to afford the desired products in good yields. Preliminary mechanism experiments showed that Ag2CO3 played an essential role in the procedure of the reaction.
Tunable and Diastereoselective Br?nsted Acid Catalyzed Synthesis of β-Enaminones
Kang, Ye-Won,Cho, Yu Jin,Han, Seung Jin,Jang, Hye-Young
supporting information, p. 272 - 275 (2016/02/03)
The Br?nsted acid catalyzed Meyer-Schuster reaction of hemiaminals was studied for the stereoselective synthesis of β-enaminones. Hemiaminals were formed from propargyl aldehydes (or the oxidation of propargyl alcohols) and amines in the presence of Br?ns
Highly stereoselective synthesis of cis-β-enaminones mediated by diethyl azodicarboxylate
Xu, Xiaoliang,Du, Ping,Cheng, Dongping,Wang, Hong,Li, Xiaonian
supporting information; experimental part, p. 1811 - 1813 (2012/02/16)
Promoted by diethyl azodicarboxylate, a novel and highly stereoselective synthesis of cis-β-enaminones via oxidative dehydrogenation and hydration of the substituted propargylamines was realized. The possible mechanism was also proposed.
Straightforward Novel One-Pot Enaminone and Pyrimidine Syntheses by Coupling-Addition-Cyclocondensation Sequences
Karpov, Alexei S.,Mueller, Thomas J. J.
, p. 2815 - 2826 (2007/10/03)
The coupling of acid chlorides 1 with terminal alkynes 2 using only one equivalent (!) of triethylamine under Sonogashira conditions followed by subsequent addition of primary or secondary amines 4 to the intermediate alkynones 3 represents a straight-for
New Entry to a Three-Component Pyrimidine Synthesis by TMS-Ynones via Sonogashira Coupling
Karpov, Alexei S.,Mueller, Thomas J. J.
, p. 3451 - 3454 (2007/10/03)
(Equation presented) TMS-ynones are versatile synthetic equivalents of β-keto aldehydes and can be readily synthesized in an atom-economical fashion by coupling (het)aroyl chlorides and (TMS)-acetylene with only one equiv (!) of triethylamine under Sonogashira conditions. This mild ynone synthesis is also a suitable entry to 2,4-disubstituted pyrimidines in the sense of a one-pot three-component reaction, i.e., a coupling-addition- cyclocondensation sequence.
Design, synthesis, and characterization of three kinds of π-cross-conjugated hexacarbenes with high-spin (S = 6) ground states
Matsuda, Kenji,Nakamura, Nobuo,Takahashi, Kazuyuki,Inoue, Katsuya,Koga, Noboru,Iwamura, Hiizu
, p. 5550 - 5560 (2007/10/02)
Three kinds of nonlinearly π-conjugated hexadiazo compounds were obtained from the corresponding hexaketones for which cyclotrimerizaton of the ethynyl ketones to form 1,3,5-triaroylbenzenes and deoxygenation of a calix[6]arene were key steps. The diazo c
A One-Pot Synthesis of β-Acylenamines
Cherif, Souheir El,Rene, Loic
, p. 138 - 140 (2007/10/02)
β-Acylenamines (β-amino α,β-unsaturated ketones) 4 are prepared in good yields in a Mannich reaction by heating a mixture of ketone 1, triethyl orthoester 2 and secondary amine 3 in a pressure vessel.
