669015-08-1Relevant academic research and scientific papers
Direct Photoexcitation of Ethynylbenziodoxolones: An Alternative to Photocatalysis for Alkynylation Reactions**
Amos, Stephanie G. E.,Cavalli, Diana,Le Vaillant, Franck,Waser, Jerome
, p. 23827 - 23834 (2021/09/25)
Ethynylbenziodoxolones (EBXs) are commonly used as radical traps in photocatalytic alkynylations. Herein, we report that aryl-substituted EBX reagents can be directly activated by visible light irradiation. They act as both oxidants and radical traps, alleviating the need for a photocatalyst in several reported EBX-mediated processes, including decarboxylative and deboronative alkynylations, the oxyalkynylation of enamides and the C?H alkynylation of THF. Furthermore, the method could be applied to the synthesis of alkynylated quaternary centers from tertiary alcohols via stable oxalate salts and from tertiary amines via aryl imines. A photocatalytic process using 4CzIPN as an organic dye was also developed for the deoxyalkynylation of oxalates.
Rh(iii)-Catalyzed olefination to build diverse oxazole derivatives from functional alkynes
He, Yuan,Zheng, Ting,Huang, Yin-Hui,Dong, Lin
supporting information, p. 4937 - 4942 (2021/06/16)
A novel Rh(iii)-catalyzed olefination reaction of oxazoles to generate diverse oxazole skeleton derivatives has been realized by directly using oxazole as the directing group. The reaction could tolerate many functional groups, affording complex oxazole derivatives with long chain alkenyls in moderate to good yields, which might find applications in the construction of diverse compounds.
Photoredox catalyzed C(sp3)[sbnd]C(sp) coupling of dihydropyridines and alkynylbenziodoxolones
Liang, Shengzong,Angnes, Ricardo A.,Potnis, Chinmay S.,Hammond, Gerald B.
supporting information, (2019/10/14)
A visible light mediated deformylative alkynylation of aldehydes is presented. Under photo irradiation, 1,4-dihydropyridine (DHP), derived from an aldehyde, generated a C(sp3)- radical which couples with an alkynylbenziodoxolone to generate an
Catalyst-Free Deaminative Functionalizations of Primary Amines by Photoinduced Single-Electron Transfer
Wu, Jingjing,Grant, Phillip S.,Li, Xiabing,Noble, Adam,Aggarwal, Varinder K.
supporting information, p. 5697 - 5701 (2019/03/21)
The use of pyridinium-activated primary amines as photoactive functional groups for deaminative generation of alkyl radicals under catalyst-free conditions is described. By taking advantage of the visible light absorptivity of electron donor–acceptor complexes between Katritzky pyridinium salts and either Hantzsch ester or Et3N, photoinduced single-electron transfer could be initiated in the absence of a photocatalyst. This general reactivity platform has been applied to deaminative alkylation (Giese), allylation, vinylation, alkynylation, thioetherification, and hydrodeamination reactions. The mild conditions are amenable to a diverse range of primary and secondary alkyl pyridiniums and demonstrate broad functional group tolerance.
Decarboxylative Negishi Coupling of Redox-Active Aliphatic Esters by Cobalt Catalysis
Liu, Xu-Ge,Zhou, Chu-Jun,Lin,Han, Xiang-Lei,Zhang, Shang-Shi,Li, Qingjiang,Wang, Honggen
, p. 13096 - 13100 (2018/09/21)
A cobalt-catalyzed decarboxylative Negishi coupling reaction of redox-active aliphatic esters with organozinc reagents was developed. The method enabled efficient alkyl–aryl, alkyl–alkenyl, and alkyl–alkynyl coupling reactions under mild reaction conditions with no external ligand or additive needed. The success of an in situ activation protocol and the facile synthesis of the drug molecule (±)-preclamol highlight the synthetic potential of this method. Mechanistic studies indicated that a radical mechanism is involved.
Redox-Activated Amines in C(sp3)-C(sp) and C(sp3)-C(sp2) Bond Formation Enabled by Metal-Free Photoredox Catalysis
Ociepa, Micha,Turkowska, Joanna,Gryko, Dorota
, p. 11362 - 11367 (2018/11/23)
The amino group represents one of the most prevalent structural motifs in organic chemistry. Therefore, application of amines as alkylating agents in synthesis is highly compelling. Herein, we present a metal-free photoredox strategy for the formation of C(sp3)-C(sp) and C(sp3)-C(sp2) bonds from redox-activated primary amine derivatives. The developed reaction of 2,4,6-triphenylpyridinium salts with alkynyl p-tolylsulfones, leading to functionalized alkynes, is easily scalable and offers broad substrate scope, high chemoselectivity, and mild conditions. Its potential is also highlighted by diversification of complex molecular scaffolds. Additionally, the approach is also suitable for synthesis of (E)-alkenes from vinyl phenyl sulfones. Mechanistic studies contribute to the elucidation of unexpected differences in reactivity of primary and secondary alkyl substituted pyridinium salts.
ARYL CARBOXAMIDE DERIVATIVES AS SODIUM CHANNEL INHIBITORS FOR TREATMENT OF PAIN
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Page/Page column 88, (2011/09/19)
The present invention provides compounds that are inhibitors of voltage-gated sodium channels (Nav), in particular Nav 1.7, and are therefore useful for the treatment of diseases treatable by inhibition of these channels, in particular, chronic pain disorders. Also provided are pharmaceutical compositions containing such compounds and processes for preparing such compounds.
HETEROCYCLIC COMPOUNDS AND USE THEREOF AS ERK INHIBITORS
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Page/Page column 223, (2009/01/23)
Disclosed are the ERK inhibitors of formula 1.0: [Formula (1.0)] and the pharmaceutically acceptable salts, esters and solvates thereof. Q is a piperidine or piperazine ring that can have a bridge or a fused ring. The piperidine ring can have a double bond in the ring. All other substitutents are as defined herein. Also disclosed are methods of treating cancer using the compounds of formula 1.0.
PYRROLIDINE DERIVATIVES AS ERK INHIBITORS
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Page/Page column 191-192, (2010/11/28)
Disclosed are the ERK inhibitors of Formula (1.0): and the pharmaceutically acceptable salts and solvates thereof. Q is a piperidine or piperazine ring that can have a bridge or a fused ring. The piperidine ring can have a double bond in the ring. All other substitutents are as defined herein. Also disclosed are methods of treating cancer using the compounds of Formula (1.0).
2,5-DIOXOIMIDAZOLIDIN-4-YL ACETAMIDES AND ANALOGUES AS INHIBITORS OF METALLOPROTEINASE MMP12.
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Page 65, (2010/02/06)
The invention provides compounds of formula (I) in which L, X, Y, Z1, Z2, R1, R2, R3 and G2 have the meanings defined in the specification; processes for their preparation; pharmaceutical c
