Journal ArticleDOI
Studies in isoxazole chemistry. III. The preparation and lithiation of 3,5-disubstituted isoxazoles
R. G. Micetich,C. G. Chin +1 more
TLDR
In this article, 3-Arylisoxazol-5-ones and 5-arylisoxozol-3-ones were prepared and converted to the N-methyl and O-methyl derivatives by reaction with diazomethane.Abstract:
3-Arylisoxazol-5-ones and 5-arylisoxazol-3-ones were prepared and converted to the N-methyl and O-methyl derivatives by reaction with diazomethane. The halogen in 3-phenyl-5-chloroisoxazole was rep...read more
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Reference EntryDOI
Heteroatom‐Facilitated Lithiations
TL;DR: A comprehensive survey of heteroatom-facilitated metalation reactions can be found in this article, where the authors classify them into two categories: alpha and beta (ortho) lithiations.
Journal ArticleDOI
A Novel Route to 5-Substituted 3-Isoxazolols. Cyclization of N,O-DiBoc β-Keto Hydroxamic Acids Synthesized via Acyl Meldrum's Acids
TL;DR: A novel and versatile three-step procedure in which carboxylic acid derivatives are converted into acyl Meldrum's acids which, upon aminolysis with N, O-bis(tert-butoxycarbonyl)hydroxylamine, lead to the N- O-diBoc-protected beta-keto hydroxamic acids.
Journal ArticleDOI
Switchable Synthesis of Pyrroles and Pyrazines via Rh(II)-Catalyzed Reaction of 1,2,3-Triazoles with Isoxazoles: Experimental and DFT Evidence for the 1,4-Diazahexatriene Intermediate.
Nikolai V. Rostovskii,Julia O. Ruvinskaya,Mikhail S. Novikov,Alexander F. Khlebnikov,Ilia A. Smetanin,Anastasiya V. Agafonova +5 more
TL;DR: 4-Aminopyrrole-3-carboxylates and pyrazine-2-car boxylates were synthesized from 5-alkoxyisoxazoles and 1-sulfonyl-1,2,3-triazoles by tuning the Rh(II) catalyst and the reaction conditions.
Book ChapterDOI
Generation and Reactions of sp2-Carbanionic Centers in the Vicinity of Heterocyclic Nitrogen Atoms
TL;DR: In this paper, the authors discuss that the generation of a carbanionic center adjacent to a neutral heteroatom such as nitrogen is often a difficult proposition and this is a consequence of several factors, of which charge repulsion by the heteroatomic lone pair, low acidity of the hydrogen to be abstracted, and undesired reaction at other reactive sites in the molecule are all major deterents.
Journal ArticleDOI
4-Halo-2-azabuta-1,3-dienes as intermediates in the rhodium carbenoid-initiated transformation of 2-halo-2H-azirines into 2,3-dihydroazetes and 2,5-dihydrooxazoles
Ilia A. Smetanin,Mikhail S. Novikov,Nikolai V. Rostovskii,Alexander F. Khlebnikov,Galina L. Starova,Dmitry S. Yufit +5 more
TL;DR: In this paper, a wide range of electron-poor 4-bromo-/4-chloro-2-azabuta-1,3-dienes were synthesized by the Rh2(OAc)4-catalyzed reaction of diazo esters and Diazo ketones with methyl 2-halo-2H-azirine-2 carboxylates.