65185-60-6Relevant academic research and scientific papers
Photocatalytic Hydroaminoalkylation of Styrenes with Unprotected Primary Alkylamines
Askey, Hannah E.,Grayson, James D.,Tibbetts, Joshua D.,Turner-Dore, Jacob C.,Holmes, Jake M.,Kociok-Kohn, Gabriele,Wrigley, Gail L.,Cresswell, Alexander J.
supporting information, p. 15936 - 15945 (2021/10/12)
Catalytic, intermolecular hydroaminoalkylation (HAA) of styrenes provides a powerful disconnection for pharmacologically relevant γ-arylamines, but current methods cannot utilize unprotected primary alkylamines as feedstocks. Metal-catalyzed HAA protocols are also highly sensitive to α-substitution on the amine partner, and no catalytic solutions exist for α-tertiary γ-arylamine synthesis via this approach. We report a solution to these problems using organophotoredox catalysis, enabling a direct, modular, and sustainable preparation of α-(di)substituted γ-arylamines, including challenging electron-neutral and moderately electron-rich aryl groups. A broad range of functionalities are tolerated, and the reactions can be run on multigram scale in continuous flow. The method is applied to a concise, protecting-group-free synthesis of the blockbuster drug Fingolimod, as well as a phosphonate mimic of itsin vivoactive form (by iterative α-C-H functionalization of ethanolamine). The reaction can also be sequenced with an intramolecularN-arylation to provide a general and modular access to valuable (spirocyclic) 1,2,3,4-tetrahydroquinolines and 1,2,3,4-tetrahydronaphthyridines. Mechanistic and kinetic studies support an irreversible hydrogen atom transfer activation of the alkylamine by the azidyl radical and some contribution from a radical chain. The reaction is photon-limited and exhibits a zero-order dependence on amine, azide, and photocatalyst, with a first-order dependence on styrene.
Transition-metal-free Intramolecular C-H amination of sulfamate esters and: N -alkylsulfamides
Kiyokawa, Kensuke,Nakamura, Shogo,Jou, Keisuke,Iwaida, Kohji,Minakata, Satoshi
supporting information, p. 11782 - 11785 (2019/10/02)
The transition-metal-free intramolecular C-H amination of sulfamate esters using iodine oxidants, tert-butyl hypoiodite (t-BuOI) and N-iodosuccinimide (NIS) is reported. A method using NIS was also successfully applied to the oxidative cyclization of N-alkylsulfamides.
meta-Selective C?H Borylation of Benzylamine-, Phenethylamine-, and Phenylpropylamine-Derived Amides Enabled by a Single Anionic Ligand
Davis, Holly J.,Genov, Georgi R.,Phipps, Robert J.
supporting information, p. 13351 - 13355 (2017/10/07)
Selective functionalization at the meta position of arenes remains a significant challenge. In this work, we demonstrate that a single anionic bipyridine ligand bearing a remote sulfonate group enables selective iridium-catalyzed borylation of a range of common amine-containing aromatic molecules at the arene meta position. We propose that this selectivity is the result of a key hydrogen bonding interaction between the substrate and catalyst. The scope of this meta-selective borylation is demonstrated on amides derived from benzylamines, phenethylamines and phenylpropylamines; amine-containing building blocks of great utility in many applications.
HETEROCYCLIC COMPOUNDS FOR THE INHIBITION OF PASK
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Page/Page column 127; 128-129, (2011/04/14)
Disclosed herein are new heterocyclic compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of inhibiting PAS Kinase (PASK) activity in a human or animal subject are also provided for the treatment of diseases such as diabetes mellitus.
Radical cyclization of ynamides into six- or eight-membered rings. Application to the synthesis of a protoberberine analog
Balieu, Sébastien,Toutah, Krimo,Carro, Laura,Chamoreau, Lise-Marie,Rousselière, Hélène,Courillon, Christine
supporting information; experimental part, p. 2876 - 2880 (2011/06/21)
A straightforward formation of six- and eight-membered rings via the radical cyclization of specifically designed ynamides is reported. This strategy provides a protoberberine analog in only three steps by a radical cyclization cascade.
RENIN INHIBITORS
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Page/Page column 29, (2009/04/25)
The present invention relates to biphenyl compounds of formula (I). These compounds are renin inhibitors of a non- peptidic nature and of low molecular weight. The invention further relates to a pharmaceutical composition containing said compounds, as wel
The development of efficient protocols for the palladium-catalyzed cyclization reactions of secondary amides and carbamates
Yang, Bryant H.,Buchwald, Stephen L.
, p. 35 - 37 (2008/02/11)
(equation presented) With the proper choice of palladium catalyst, ligand, and base, five-, six-, and seven-membered rings are formed efficiently from secondary amide or secondary carbamate precursors, offering significant improvements to currently existing methodology.
Intramolecular palladium-catalyzed aryl amination and aryl amidation
Wolfe, John P.,Rennels, Roger A.,Buchwald, Stephen L.
, p. 7525 - 7546 (2007/10/03)
Upon treatment with a palladium catalyst and a suitable base, aromatic halides undergo intramolecular substitution to form five, six, and seven-membered rings. In a similar fashion aryl halides with pendant amides or sulfonamides are cyclized to form five and six-membered rings.
The Asymmetric Synthesis of 1-Alkyl-2,3,4,5-Tetrahydro-Benzazepines and Benzo-1-AzabicycloDecanes
Meyers, A. I.,Hutchings, Richard H.
, p. 1807 - 1820 (2007/10/02)
The metalation-alkylation of benzazepine formamidines gives high yields and good diastereoselectivity of 1-substituted derivatives.Removal of the chiral auxiliary leads to the title compounds in 84-96 percent ee and represents the first chiral benzazepine
