697-87-0Relevant academic research and scientific papers
Revisiting the Gold-Catalyzed Dimerization of 2-Ethynylanilines: A Room-Temperature and Silver-Free Protocol for the Synthesis of Multifunctional Quinolines
Praveen, Chandrasekar,Perumal
, p. 855 - 864 (2016/03/15)
A room temperature and silver-free protocol for the formation of quinolines from 2-ethynylanilines through a dimerization event was achieved using a dinuclear gold catalyst, Au2(BIPHEP)(NTf2)2. The reaction is inherently modular, allowing for the incorporation of peripheral substituents at any site of the quinoline product. The reaction is readily applied to other heterocyles also as exemplified by the preparation of naphthyridines. Competition reactions to determine the reactivity of dissimilar alkynes demonstrated that the product ratio of dimerization vs intermolecular addition is rather dependent on the electronic nature of aryl substituent on the alkynes. However, control experiments with substrates possessing internal alkynes resulted in cycloisomerization instead of expected dimerization, which is indicative of possible steric influence of the alkyne terminus in the reaction outcome.
Asymmetric radical and anionic cyclizations of axially chiral carbamates
Guthrie, David B.,Curran, Dennis P.
supporting information; experimental part, p. 249 - 251 (2009/06/28)
Standard Boc, Alloc, and Cbz derivatives of N-2,4-dimethyl-6-iodophenyl-N- allyl anilines are axially chiral and can be readily resolved into atropisomers whose racemization barriers exceed 30 kcal/mol. The resolved axially chiral carbamates undergo radic
Polymer-supported organotin reagents for regioselective halogenation of aromatic amines
Chretien, Jean-Mathieu,Zammattio, Francoise,Le Grognec, Erwan,Paris, Michael,Cahingt, Blanche,Montavon, Gilles,Quintard, Jean-Paul
, p. 2870 - 2873 (2007/10/03)
(Chemical Equation Presented) Polymer-supported triorganotin halides were used in the halogenation reaction of aromatic amines. Treatment of aromatic amines with n-butyllithium and polymer-supported organotin halides gave the corresponding polymer-bound N-triorganostannylamines, which by treatment with bromine or iodine monochloride gave the para-halogenated aromatic amines with high yields and high selectivities. The polymer-supported organotin halides reagents regenerated during the course of the halogenation reaction can be reused without loss of efficiency. The presence of tin residues in halogenated aromatic amines was also investigated and evaluated at under 20 ppm after three runs.
Synthesis of polyfunctional indoles and related heterocycles mediated by cesium and potassium bases
Koradin, Christopher,Dohle, Wolfgang,Rodriguez, Alain L.,Schmid, Bertram,Knochel, Paul
, p. 1571 - 1587 (2007/10/03)
A general preparation of 2-substituted indoles starting from functionalized 2-alkynylanilines has been developed. This base mediated reaction has also been used to synthesize the heterocyclic core of the marine alkaloid hinckdentine A. Furthermore the reaction was successfully adapted to the solid phase. Benzofurans and isoindolones could also be prepared with this method.
Synthesis of Polyfunctionalized Biphenyls as Intermediates for a New Class of Liquid Crystals
Manka, Jason T.,Guo, Fengli,Huang, Jianping,Yin, Huiyong,Farrar, John M.,Sienkowska, Monika,Benin, Vladimir,Kaszynski, Piotr
, p. 9574 - 9588 (2007/10/03)
A series of hexa- and octasubstituted biphenyls containing halogen, amino, nitro, and propylthio substituents were prepared by metal-mediated convergent synthesis from halobenzene precursors. The Pd-assisted C-C coupling methods were ineffective in the fo
