23438-23-5Relevant articles and documents
Target analysis of α-alkylidene-γ-butyrolactones in uropathogenic E. coli
Kunzmann, Martin H.,Sieber, Stephan A.
, p. 3061 - 3067,7 (2012)
α-Alkylidene-γ-butyrolactones are quite common in nature and exhibit a broad spectrum of biological activities. We therefore synthesized a small library of xanthatine inspired α-alkylidene-γ-butyrolactones to screen non-pathogenic and uropathogenic E. col
On the addition of .OH radicals to the ipso positions of alkyl-substituted aromatics: Production of 4-hydroxy-4-methyl-2,5-cyclohexadien-1-one in the radiolytic oxidation of p-cresol
Schuler, Robert H.,Albarran, Guadalupe,Zajicek, Jaroslav,George,Fessenden, Richard W.,Carmichael, Ian
, p. 12178 - 12183 (2002)
4-Hydroxy-4-methyl-2,5-cyclohexadien-1-one has been conclusively identified by its 1H and 13C NMR spectra as a significant initial product in the radiolysis of aqueous solutions of p-cresol. This product is formed as the result of ox
Substrate-Selectivity in Catalytic Photooxygenation Processes Using a Quinine-BODIPY System
Coeffard, Vincent,Fischer, Jér?me,Nun, Pierrick,Serier-Brault, Hélène
, p. 463 - 468 (2020)
Substrate selectivity by means of synthetic catalysts remains a challenging topic in chemistry. Here, a catalytic system combining an iodo-BODIPY photosensitizer and quinine was evaluated in the competitive photooxygenation of non-hydrogen and hydrogen-bond-donor substrates. The ability of quinine to activate hydrogen-bond-donor substrates towards photooxygenation was reported and the results were benchmarked with photooxygenation experiments in the absence of quinine.
Quinone Alkylation Using Organocadmium Reagents: A General Synthesis of Quinols
Aponick, Aaron,McKinley, Jason D.,Raber, Jeffrey C.,Wigal, Carl T.
, p. 2676 - 2678 (1998)
Reactions of p-benzoquinone with organocadmium reagents yield quinols, the result of quinone carbonyl monoalkylation. The reactions proceed in good yield and are devoid of bisaddition and hydroquinone byproducts. Quinone alkylations using this method show
Reactions of p-Quinols with Aldehydes and Imines: Stereoselective Access to Polyheterobicyclic and Tricyclic Systems
García-García, Carolina,Redondo, María C.,Ribagorda, María,Carre?o, M. Carmen
, p. 7377 - 7388 (2014)
Dihydrobenzo[1,3]dioxolanones, tetrahydrobenzo[d]oxazolones and heterotricyclic derivatives have been stereoselectively synthesized from p-quinols upon reaction with aldehydes or benzaldimines under basic catalysis. Reactions occurred in an experimentally
Redox-neutral functionalization of α-Csp3-H bonds of secondary cyclic amines: a highly atom-economical strategy forN-arylation/formal cross-dehydrogenative couplings
Husen, Saddam,Jha, Priyankar,Kumar, Ravindra
supporting information, p. 2950 - 2955 (2021/05/05)
An efficient redox-neutral method has been developed for α-Csp3-H functionalization of secondary cyclic aminesviaconcurrentN-arylation/formal cross dehydrogenation coupling (CDC) with sp2-C-H and sp3-C-H bonds of arenes an
Multigram Synthesis of Trioxanes Enabled by a Supercritical CO2Integrated Flow Process
Wu, Lingqiao,Abreu, Bruna L.,Blake, Alexander J.,Taylor, Laurence J.,Lewis, William,Argent, Stephen P.,Poliakoff, Martyn,Boufroura, Hamza,George, Michael W.
supporting information, p. 1873 - 1881 (2021/07/21)
Photochemical synthesis of highly reactive hydroperoxides and their conversion into useful products, such as 1,2,4-trioxanes, are of wide interest for synthetic organic chemistry and pharmaceutical manufacturing particularly because of their relevance as potential antimalarial and anticancer treatment drugs, for example, Artemisinin. One class of antimalarial drugs is based on 1,2,4-trioxane scaffolds although production of such compounds on a gram scale is challenging due to their instability in oxidizable solvents. Furthermore, current methods employ either solid oxidants, which make continuous processing problematic, or molecular oxygen, requiring long reaction times of up to 48 h. Here, we report a new multigram continuous approach using a custom-built high-pressure sapphire photoreactor to synthesize trioxanes via the dearomatization of para-substituted phenols by photogenerated singlet oxygen in supercritical CO2. CO2 also facilitates mixing with O2 and has lower viscosity, thereby improving penetration into the pores of the solid acid catalyst used for the formation of trioxanes. We show the capabilities of a 5.2 mL reactor to scale up the reaction to 67 g/day. This synthetic approach provides a platform to rapidly access high-value compounds under flow conditions, with high atom efficiencies, excellent yields, short reaction times, and without the need for isolation of hazardous intermediates.
Reductive Aromatization of Quinols with B2pin2 as Deoxidizing Agent
Liu, Bin,Xu, Yin,Luo, Zhibin,Xie, Jimin
supporting information, p. 1022 - 1024 (2020/03/19)
We have demonstrated B2pin2 as superior deoxidizing agent for the reductive deoxygenation of quinol derivatives under basic conditions. A wide range of highly functionalized phenols were obtained in good yields including a complex drug molecule, which revealed the high functional group tolerance of this protocol.
Phosphine-Catalyzed Cascade Michael Addition/[4+2] Cycloaddition Reaction of Allenoates and 2-Arylidene-1,3-indanediones
Shi, Wangyu,Mao, Biming,Xu, Jiaqing,Wang, Qijun,Wang, Wei,Wu, Yongjun,Li, Xuefeng,Guo, Hongchao
supporting information, p. 2675 - 2680 (2020/03/26)
The phosphine-catalyzed cascade Michael addition/[4+2] cycloaddition reaction of tetrahydrobenzofuranone-derived allenoates and 2-arylidene-1,3-indanediones has been reported, affording spirocyclic 1,3-indanedione derivatives in moderate to high yields wi
Site-selective 1,3-double functionalization of arenes using: Para -quinol, C-N, and C-C/C-P three-component coupling
Husen, Saddam,Chauhan, Anil,Kumar, Ravindra
supporting information, p. 1119 - 1124 (2020/03/11)
A catalytic and site-selective approach has been demonstrated for dual functionalization of arenes via cross-coupling reactions of p-quinols with amines and isocyanides/phosphites. The strategy enables the production of a series of 3-amino-benzamides and
