Nitrile Oxide, Alkenes, Dipolar Cycloaddition, Isomerization and Metathesis Involved in the Syntheses of 2-Isoxazolines

Molecules, Journal Year: 2023, Volume and Issue: 28(6), P. 2547 - 2547

Published: March 10, 2023

The involvement of 1,3-dipolar cycloaddition (1,3-DP), double bond migration, metathesis, and nitrile oxide (including in situ-generated oxide) as dipoles, together with the C=C containing dipolarophiles, syntheses 2-isoxazolines is presented. Methods for synthesizing isoxazolines (other than 1,3-DP cycloaddition) were also presented briefly. Various methods preparation, especially procedures, are Special attention was paid to application various combinations migration (DBM) alkene metathesis (AM) trisubstituted isoxazolines. Allyl compounds type QCH2CH=CH2 (Q = ArO, ArS, Ar, others) play role dipolarophile precursors DPC mentioned, DBM AM. Mechanistic aspects cycloadditions, i.e., concerted or stepwise reaction mechanism their regio- stereoselectivity discussed from experimental theoretical points view. Side reactions accompanying cycloaddition, dimerization, considered. 2-Isoxazoline applications organic synthesis biological activity, broad utility medicine, agriculture, other fields raised. Some remaining challenges field finally discussed.

Language: Английский

Versatile Diazomethane Sulfonamide for Expedited Exploration of Azole‐Based Carbonic Anhydrase Inhibitors via [3+2] Cycloaddition

ChemMedChem, Journal Year: 2023, Volume and Issue: 18(10)

Published: April 12, 2023

Abstract A newly introduced diazo reagent, 1‐diazo‐ 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 the sulfonamide chemical space highly relevant but hitherto not investigated in context inhibition therapeutically isoforms carbonic anhydrase enzyme. Using this three sets based on pyrazole, 1,2,3‐triazole and tetrazole cores were synthesized profiled for tumor‐associated h CA IX XII as well abundant cytosolic I II isoforms. virtual library design docking prioritization tool Schrödinger suite, one promising leads was evolved into dual IX/XII inhibitor with excellent selectivity over off‐target II. The new synthetic strategy will support discovery novel, isoform‐selective inhibitors within poorly explored azole space.

Language: Английский

Synthesis and Reactivity of α-Diazo-β-keto Sulfonamides

Synthesis, Journal Year: 2024, Volume and Issue: unknown

Published: June 19, 2024

Abstract Copper-mediated reactions of α-diazo-β-keto sulfonamides led to a range products, including alkynesulfonamides, enamines, and α-halosulfonamides, with no evidence for intramolecular C–H insertion in any the reactions, contrast reactivity comparable α-diazo-β-oxo sulfones. Use copper(II) triflate (5 mol%) isolation series alkynesulfonamides (up 12% yield) enamines 64% yield). chloride formation, addition, α-halosulfonamides; use stoichiometric amounts chloride/bromide enabled facile halogenation β-keto sulfonamide form α-halosulfonamides 63%

Language: Английский