- R4NHal/NOHSO4: A Usable System for Halogenation of Isoxazoles, Pyrazoles, and beyond
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A new convenient and versatile halogenating system (R4NHal/NOHSO4), giving straightforward and general access to halogenated 3,5-diaryl- and alkylarylisoxazoles, pyrazoles and electron-rich benzenes from the corresponding scaffolds, is suggested. The method provides excellent regioselectivity, scalability to the gram scale, and a broad scope for both aromatics and halogens. A three-step, one-pot reaction protocol was developed, and a series of 3,5-diaryl-4-haloisoxazoles has been efficiently synthesized from 1,2-diarylcyclopropanes under suggested nitrosating-halogenating conditions.
- Bondarenko, Oksana B.,Karetnikov, Georgy L.,Komarov, Arseniy I.,Pavlov, Aleksandr I.,Nikolaeva, Svetlana N.
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supporting information
p. 322 - 332
(2021/01/14)
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- Isomerizable (: E / Z)-alkynyl- O -methyl oximes employing TMSCl-NCS in chlorinative cyclization for the direct synthesis of 4-chloroisoxazoles
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For the first time, 4-chloroisoxazoles are directly synthesized in moderate to excellent yields from (E/Z)-alkynyl-O-methyl oximes via chlorinative cyclization. The synthesis employs the combination of N-chlorosuccinimide (NCS) and chlorotrimethylsilane (
- Kaewsri, Wilailak,Thongsornkleeb, Charnsak,Tummatorn, Jumreang,Ruchirawat, Somsak
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p. 48666 - 48675
(2016/06/09)
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- Chiral Mercaptoacetamides Display Enantioselective Inhibition of Histone Deacetylase6 and Exhibit Neuroprotection in Cortical Neuron Models of Oxidative Stress
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Mercaptoacetamide-based ligands have been designed as a new class of histone deacetylase (HDAC) inhibitors for possible use in the treatment of neurodegenerative diseases. The thiol group of these compounds provides a key binding element for interaction with the catalytic zinc ion, and thus differs from the more typically employed hydroxamic acid based zinc binding groups. Herein we disclose the chemistry and biology of some substituted mercaptoacetamides with the intention of increasing HDAC6 isoform selectivity while maintaining potency similar to their hydroxamic acid analogues. The introduction of a stereocenter α to the thiol group was found to have a considerable impact on HDAC inhibitor potency. These new compounds were also profiled for their therapeutic potential in an invitro model of stress-induced neuronal injury and were found to act as nontoxic neuroprotective agents.
- Kalin, Jay H.,Zhang, Hankun,Gaudrel-Grosay, Sophie,Vistoli, Giulio,Kozikowski, Alan P.
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experimental part
p. 425 - 439
(2012/06/04)
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- The synthesis of highly substituted isoxazoles by electrophilic cyclization: An efficient synthesis of valdecoxib
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(Chemical Equation Presented) A large number of functionally substituted 2-alkyn-1-one O-methyl oximes have been cyclized under mild reaction conditions in the presence of ICl to give the corresponding 4-iodoisoxazoles in moderate to excellent yields. The resulting 4-iodoisoxazoles undergo various palladium-catalyzed reactions to yield 3,4,5-trisubstituted isoxazoles, including valdecoxib.
- Waldo, Jesse P.,Larock, Richard C.
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p. 9643 - 9647
(2008/03/17)
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- Synthesis of 4-isoxazoleboronic acids: A new route to 4-isoxazolones
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4-Isoxazoleboronic acids have been prepared by interaction of 4-isoxazolylmagnesium iodides with trimethyl borate. Some of their reactions are described; in particular oxidative deboronation represents a new useful route to 4-isoxazolones.
- Cogoli, Augusto,Gruenanger, Paolo
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