Polyhalogenated 2‐Azabicyclo[2.2.1]heptanes from Polyhaloaldimines and Cyclopentadiene via Cycloaddition and Wagner‐Meerwein Rearrangement
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DOI: 10.1002/ajoc.202400017
Abstract: 2‐Arylsulfonyl‐2‐azabicyclo[2.2.1]hept‐5‐enes, synthesized via the cycloaddition of chloral‐ or dichloro(phenyl)acetaldehyde N‐arylsulfonylimines to cyclopentadiene, undergo Wagner‐Meerwein rearrangement under the action of bromine or chlorine to afford 3‐polychloro‐6,7‐dyhalogenated 2‐arylsulfonylazabicyclo[2.2.1]heptanes. read more here.
Keywords: meerwein rearrangement; wagner meerwein; via cycloaddition; polyhalogenated azabicyclo ... See more keywords
Versatile Diazomethane Sulfonamide for Expedited Exploration of Azole‐Based Carbonic Anhydrase Inhibitors via [3+2] Cycloaddition
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DOI: 10.1002/cmdc.202200607
Abstract: A newly introduced diazo reagent, 1‐diazo‐N,N‐bis(4‐methoxybenzyl)methanesulfonamide, enables access to a range of azole‐based primary sulfonamides via [3+2] cycloaddition followed by protecting group removal. Such compounds are representative of the sulfonamide chemical space highly relevant but… read more here.
Keywords: azole based; via cycloaddition; carbonic anhydrase;
The synthesis of isoxazolo[2,3-c]quinazolines via a cycloaddition of quinazoline-3-oxides and acrylates
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DOI: 10.1016/j.tetlet.2020.151818
Abstract: Abstract A variety of isoxazolo[2,3-c]quinazolines were synthesized via a [3 + 2] cycloaddition of quinazoline-3-oxides with acrylates. The reaction exhibits a broad substrate scope and good functional group tolerance. The corresponding isoxazolo[2,3-c]quinazolines can be obtained in good… read more here.
Keywords: oxides acrylates; quinazoline oxides; cycloaddition quinazoline; via cycloaddition ... See more keywords
Elementary Steps in Olefin Metathesis: Nickelacyclobutanes via Cycloaddition to Nickel Carbenes
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DOI: 10.1021/jacs.5c06505
Abstract: Olefin metathesis and cyclopropanation, major reactions in the synthetic toolbox, are predominantly catalyzed by platinum-group metals. First-row transition metal alternatives are desirable from the perspective of supply-chain sustainability. Although cyclopropanation by nickel catalysts is well… read more here.
Keywords: metathesis; elementary steps; nickel; olefin metathesis ... See more keywords
A new access to diazaphospholes via cycloaddition-cycloreversion reactions on triazaphospholes.
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DOI: 10.1039/d2cc02269a
Abstract: A novel bis-CF3-substituted diazaphosphole was synthesized selectively from hexafluoro-2-butyne and a 3H-1,2,3,4-triazaphosphole derivative. The [4+2] cycloaddition and subsequent cycloreversion reaction under elimination of pivaloyl nitrile affords the product in high yield. The heterocycle coordinates via… read more here.
Keywords: cycloreversion; diazaphospholes via; via cycloaddition; new access ... See more keywords
Syntheses of highly functionalized cyclobutenes via [2+1+1] cycloaddition of isocyanides and an unprecedented ring expansion
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DOI: 10.1039/d4qo01518e
Abstract: A new type of Lewis acid catalytic [2+1+1] cycloaddition reactions of isocyanides with alkylidene malonates and 3‑alkylideneindolinones were reported herein. The method exhibited the easily accessible starting materials, broad substrate... read more here.
Keywords: syntheses highly; cyclobutenes via; functionalized cyclobutenes; highly functionalized ... See more keywords
Regioselective Synthesis of 5-Trifluoromethyl 1,2,4-Triazoles via [3 + 2]-Cycloaddition of Nitrile Imines with CF3CN
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DOI: 10.3390/molecules27196568
Abstract: We herein describe a general approach to 5-trifluoromethyl 1,2,4-triazoles via the [3 + 2]-cycloaddition of nitrile imines generated in situ from hydrazonyl chloride with CF3CN, utilizing 2,2,2-trifluoroacetaldehyde O-(aryl)oxime as the precursor of trifluoroacetonitrile. Various functional… read more here.
Keywords: triazoles via; via cycloaddition; trifluoromethyl triazoles; cycloaddition nitrile ... See more keywords