Fast, easy, solvent-free, microwave-promoted Michael addition of anilines to α,β-unsaturated alkenes: synthesis of N-aryl functionalized β-amino esters and acids
The rapid, simple, microwave-promoted synthesis of N-aryl functionalized β-amino esters using Michael addition reactions is presented. Reactions are performed neat at 200 °C for 20 min and are catalyzed by acetic acid. The esters can be easily hydrolyzed to the corresponding N-aryl functionalized β-amino acids.
Amore, Kristen M.,Leadbeater, Nicholas E.,Miller, Tyson A.,Schmink, Jason R.
HOTf-catalyzed intermolecular hydroamination reactions of alkenes and alkynes with anilines
Herein, the intermolecular hydroamination of alkenes and alkynes with anilines catalyzed by HOTf under mild conditions has been developed. This reaction provides one of the simplest alkene and alkyne addition methods and is an alternative to metal-catalyzed reactions. At the same time, the intramolecular hydroamination of alkynes with anilines proceeds smoothly to obtain quinolines. We found that this strategy is efficient in building complex structures from simple starting materials in an environmentally benign fashion.
Xu, Xuefeng,Zhang, Xu,Wang, Zhiqiang,Kong, Manman
p. 40950 - 40952
(2015/05/20)
Boric acid/glycerol as an efficient catalyst for synthesis of thiomorpholine 1,1-dioxide by double michael addition reaction in water
Thiomorpholine 1,1-dioxides were prepared with double Michael addition reaction of aromatic amines to divinyl sulfone catalyzed by boric acid/glycerol in water. This catalyst system was also used for the Michael addition reaction of aromatic amines to electron-deficient alkenes. The reaction is simple and green and gives good to excellent yields.
Halimehjnai, Azim Ziyaei,Hosseyni, Seyedmorteza,Gholami, Hadi,Hashemi, Mohammed M.
p. 191 - 197,7
(2020/09/02)
Tetrahydroquinolines by lewis acid-promoted friedel-crafts cyclizations
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Bunce, Richard A.,Cain, Nicholas R.,Cooper, John G.
p. 28 - 43
(2013/03/14)
Assessment and use of two silicon carbide multi-well plates for library synthesis and proteolytic digests using microwave heating
The use of two silicon carbide plates is reported for the preparation of three libraries of organic molecules using microwave heating. In addition, a preliminary study has been carried out, showing that one of the plates can also be used in a proteomics setting. Both the 24-position and 48-position plates heated evenly when irradiated with microwave energy. The 48-position plate was used to prepare a library of N-aryl functionalized β-amino esters via an aza-Michael reaction between anilines and Michael acceptors. The 24-position plate was used to prepare a library of biaryls via a Suzuki coupling methodology and a library of 1,4-dihydropyridines via a Hantzsch synthesis. The 48-position plate was also used to perform the proteolytic digestion of insulin chain B by trypsin. The Royal Society of Chemistry 2009.
Stencel, Lauren M.,Kormos, Chad M.,Avery, Keri B.,Leadbeater, Nicholas E.
experimental part
p. 2452 - 2457
(2009/09/26)
Use of a scientific microwave apparatus for rapid optimization of reaction conditions in a monomode function and then substrate screening in a multimode function
Recently, a new apparatus has become available, which aims to bring together in one unit the advantages of a monomode and a multimode microwave device. We have assessed the applicability of the apparatus toward rapid optimization of reaction conditions in a monomode function and then substrate screening in a multimode function. We have also probed the effects of differences in microwave absorptivity of reaction mixtures on the product conversions in screening multiple substrates simultaneously in a multimode microwave apparatus. We find that when the microwave absorptivity of a reaction mixture is dictated by the solvent, there is little effect on the heating profile of varying the substrate in a screening run. However, this is not the case when reactions involving non-microwave absorbant solvents are used. In this case the characteristics of the substrate can affect significantly the outcome of the reaction.
Leadbeater, Nicholas E.,Schmink, Jason R.
p. 6764 - 6773
(2008/02/07)
Ring-expansion of some heterocyclic β-ketoesters with dimethyl acetylene dicarboxylate. Part 2
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McHugh, Michael,Proctor, George R.
p. 2230 - 2253
(2007/10/02)
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