Synthesis of 2‐(1H‐Azol‐1‐ylmethyl)phenols from ortho‐Quinone Methide Precursors and NH‐Azoles under Solvent‐ and Catalyst‐free Conditions
Sign Up to like & getrecommendations! Published in 2025 at "Asian Journal of Organic Chemistry"
DOI: 10.1002/ajoc.202500039
Abstract: We have developed a non‐catalytic method for the ortho‐hydroxybenzylation of NH‐azoles that differ significantly in nucleophilicity and basicity (imidazoles, benzimidazoles, pyrazoles and others) with ortho‐quinone methide precursors (salicylic alcohols and phenolic Mannich bases) in the… read more here.
Keywords: synthesis azol; quinone methide; methide precursors; ortho quinone ... See more keywords
Investigations on Superbase Mediated Reactivity of N‐Tosylhydrazones with Aza‐ortho‐Quinone Methide Precursors
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DOI: 10.1002/ejoc.202400151
Abstract: We have encountered a superbase‐mediated chemoselective reaction of N‐tosylhydrazones with aza‐ortho‐quinone methide precursors. When tosylhydrazone was treated with ortho‐aminobenzyl alcohol in super basic conditions (KOH+DMSO), we observed the formation of 2‐substituted quinoline. The reaction was… read more here.
Keywords: aza ortho; ortho quinone; quinone methide; superbase mediated ... See more keywords
Oxidation with a “Stopover” – Stable Zwitterions as Intermediates in the Oxidation of α‐Tocopherol (Vitamin E) Model Compounds to their Corresponding ortho‐Quinone Methides
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DOI: 10.1002/open.202000306
Abstract: Abstract As a prominent member of the vitamin E group, α‐tocopherol is an important lipophilic antioxidant. It has a special oxidation chemistry that involves phenoxyl radicals, quinones and quinone methides. During the oxidation to the… read more here.
Keywords: quinone methide; oxidation; quinone methides; rotation ... See more keywords
1,6-Conjugate addition of C-nucleophiles to p-quinone methide surrogate: Synthesis of diarylpropanes
Sign Up to like & getrecommendations! Published in 2019 at "Tetrahedron"
DOI: 10.1016/j.tet.2018.12.048
Abstract: Abstract 1,6-Conjugate addition of various carbon nucleophiles to p-quinone methide surrogate is reported. The active methylene containing C-nucleophiles such as 1,3-diketones, diesters and ketoesters underwent two consecutive additions leading to bis-addition products, diarylpropanes. Whereas, nitroalkanes… read more here.
Keywords: conjugate addition; nucleophiles quinone; synthesis; addition ... See more keywords
o-Quinone methide with overcrowded olefinic core as a catalytically-active surrogate of triarylmethylium salt for dehydridative oxidation of benzylic alcohols under aerobic photoirradiation conditions
Sign Up to like & getrecommendations! Published in 2021 at "Tetrahedron"
DOI: 10.1016/j.tet.2021.132459
Abstract: Abstract An o-quinone methide (o-QM) competent as a catalyst for the dehydridative oxidation of benzylic alcohols was developed. The introduction of an overcrowded olefinic component into the o-QM induced structural distortion, beneficial for imparting triarylmethylium… read more here.
Keywords: quinone methide; dehydridative oxidation; oxidation benzylic; benzylic alcohols ... See more keywords
Mammalian Esterase Activity: Implications for Peptide Prodrugs.
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DOI: 10.1021/acs.biochem.4c00446
Abstract: As a traceless, bioreversible modification, the esterification of carboxyl groups in peptides and proteins has the potential to increase their clinical utility. An impediment is the lack of strategies to quantify esterase-catalyzed hydrolysis rates for… read more here.
Keywords: quinone methide; esterase; esterase activity; methide elimination ... See more keywords
PNA Conjugates of Quinone Methide Precursors Alkylate RNA after Activation with Light.
Sign Up to like & getrecommendations! Published in 2020 at "Bioconjugate chemistry"
DOI: 10.1021/acs.bioconjchem.9b00796
Abstract: Quinone methide precursors 2 and 3 were protected with a photoreactive 2-nitrobenzyl group and conjugated to peptide nucleic acids (PNA) using a Huisgen click reaction. After brief irradiation at 365 nm, crosslinking with com-plementary RNA… read more here.
Keywords: quinone methide; alkylate rna; methide precursors; precursors alkylate ... See more keywords
Metabolic Activation of Militarine In Vitro and In Vivo.
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DOI: 10.1021/acs.chemrestox.1c00430
Abstract: Bletilla striata is consumed as food and herbal medicine. Militarine (MLT) is a major ingredient in B. striata. Previous studies demonstrated that MLT showed teratogenic toxicity to zebrafish embryos. The present study aimed to identify… read more here.
Keywords: activation militarine; metabolic activation; militarine; quinone methide ... See more keywords
Nonenzymatic Self-Assembly Access to Diverse ortho-Quinone Methide-Based Pseudonatural Products.
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DOI: 10.1021/acs.orglett.2c02268
Abstract: A nonenzymatic self-assembly program was introduced to explore diverse clavatol-based pseudonatural products (PNPs) in a marine-derived fungus. Intermolecular couplings of the chemoreactive ortho-quinone methide of clavatol with native acceptors led to 14 clavatol-based PNPs with… read more here.
Keywords: nonenzymatic self; based pseudonatural; self assembly; pseudonatural products ... See more keywords
Aza-ortho-Quinone Methide Promoted Strain-Release-Driven Conversion of Azabicyclo[1.1.0]butanes into Functionalized Azetidines.
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DOI: 10.1021/acs.orglett.4c03577
Abstract: A strategy for activating azabicyclo[1.1.0]butane (ABB) with in situ generated aza-ortho-quinone methide, promoted by HFIP, is reported. This unified activation, vis-à-vis strain-release-driven N/C3-functionalization, features a new means to prepare functionalized azetidines from ABB. Additionally, the… read more here.
Keywords: strain release; quinone methide; methide promoted; ortho quinone ... See more keywords
4-Amidophenol Quinone Methide Precursors: Effective and Broad-Scope Nonoxime Reactivators of Organophosphorus-Inhibited Cholinesterases and Resurrectors of Organophosphorus-Aged Acetylcholinesterase.
Sign Up to like & getrecommendations! Published in 2024 at "ACS chemical neuroscience"
DOI: 10.1021/acschemneuro.4c00011
Abstract: Acetylcholinesterase (AChE) inhibition by organophosphorus (OP) compounds poses a serious health risk to humans. While many therapeutics have been tested for treatment after OP exposure, there is still a need for efficient reactivation against all… read more here.
Keywords: quinone methide; methide precursors; reactivation; broad scope ... See more keywords