309974-70-7Relevant academic research and scientific papers
Green Organocatalytic Synthesis of Indolines and Pyrrolidines from Alkenes
Theodorou, Alexis,Kokotos, Christoforos G.
, p. 1577 - 1581 (2017/05/05)
Employing a green and efficient 2,2,2-trifluoroacetophenone-catalyzed oxidation of alkenes, which utilizes H2O2 as the green oxidant, a novel and sustainable synthesis of indolines and pyrrolidines was developed. This constitutes a cheap, general and environmentally-friendly protocol for the synthesis of substituted nitrogen-containing heterocycles. A variety of substitution patterns, both aromatic and aliphatic moieties, are well tolerated leading to the desired nitrogen heterocycles in good to excellent yields. (Figure presented.).
Pd(0)-catalyzed alkene oxy- and aminoalkynylation with aliphatic bromoacetylenes
Nicolai, Stefano,Sedigh-Zadeh, Raha,Waser, Jeroime
, p. 3783 - 3801 (2013/06/26)
Tetrahydrofurans and pyrrolidines are among the most important heterocycles found in bioactive compounds. Cyclization-functionalization domino reactions of alcohols or amines onto olefins constitute one of the most efficient methods to access them. In this context, oxy- and aminoalkynylation are especially important reactions, because of the numerous transformations possible with the triple bond of acetylenes, yet these methods have been limited to the use of silyl protected acetylenes. Herein, we report the first palladium-catalyzed oxy- and aminoalkynylation using aliphatic bromoalkynes, which proceeded with high diastereoselectivity and functional group tolerance. A one-pot hydrogenation of the triple bond gave then access to alkyl-substituted tetrahydrofurans and pyrroldines. Finally, a detailed study of the side products formed during the reaction gave a first insight into the reaction mechanism.
Palladium(II)-catalyzed oxidative cascade cyclization reactions of anilides and anilines: Scope and mechanistic investigations
Yip, Kai-Tai,Yang, Dan
, p. 2166 - 2175 (2011/10/12)
With Pd(OAc)2/pyridine as the catalyst system and molecular oxygen as a green oxidant, acrylanilides and N-allylanilines undergo oxidative cascade cyclization to form heterocyclic rings in high yields. This methodology is applicable to acrylani
The attempted stereoselective synthesis of chiral 2,2′-biindoline
Gresser, Mary J.,Wales, Steven M.,Keller, Paul A.
experimental part, p. 6965 - 6976 (2010/09/18)
The attempted first stereoselective synthesis of 2,2′-biindoline using a metathesis-Sharpless asymmetric dihydroxylation strategy results in the synthesis of the heterocycle in poor to modest stereoselectivity. Attempts to improve the ee by varying the he
Curtius rearrangement of aromatic carboxylic acids to access protected anilines and aromatic ureas
Lebel, Helene,Leogane, Olivier
, p. 5717 - 5720 (2007/10/03)
(Diagram presented) The reaction of a chloroformate or di-tert-butyl dicarbonate and sodium azide with an aromatic carboxylic acid produces the corresponding acyl azide, presumably through the formation of an azidoformate. The acyl azide undergoes a Curtius rearrangement to form an isocyanate derivative which is trapped either by an alkoxide or by an amine to form the aromatic carbamate or urea. The reaction conditions are compatible with a variety of functional groups and allow the synthesis of a number of aniline derivatives containing alkyl, halide, nitro, ketone, ether, and thioether substituents.
Construction of nitrogen-heterocyclic compounds through zirconium mediated intramolecular alkene-carbonyl coupling reaction of N-(o-alkenylaryl)carbamate derivatives
Takigawa, Yasushi,Ito, Hisanaka,Omodera, Katsunori,Ito, Maiko,Taguchi, Takeo
, p. 1385 - 1392 (2007/10/03)
Intramolecular alkene-carbonyl coupling reaction of N-benzyl-N-(o- alkenylaryl)carbamate derivative derived from o-aminostyrene, o-(aminomethyl)styrene and o-aminoallylbenzene smoothly proceeded by treating with zirconocene-butene complex to give the corresponding lactam derivative.
Combined directed ortho metalation - Grubbs metathesis tactics. Synthesis of benzazepine, benzazocine, and benzannulated 7-, 8-, 9-, and 15-membered ring sulfonamide heterocycles
Lane,Snieckus
, p. 1294 - 1296 (2007/10/03)
The rapid construction of diverse benzannulated heterocyclic systems 7, 8, 12a-c, 15a-b, and 21 using Directed ortho Metalation - Ring Closure Metathesis sequences is reported.
