Conjugate Addition of 3‐Aryl Oxindoles to in situ generated o‐ Quinone Methides Without Essential Electronic or Steric Groups
Sign Up to like & getrecommendations! Published in 2024 at "Asian Journal of Organic Chemistry"
DOI: 10.1002/ajoc.202400370
Abstract: Herein an efficient method for in situ generated o‐quinone methides without essential electronic or steric groups at the exocyclic methylene or on six‐membered ring was established. The method relies on acetylation of salicylylols and subsequently base promoted 1,4‐elimination. The in situ generated o‐quinone methides could… read more here.
Keywords: situ generated; generated quinone; quinone methides; without essential ... See more keywords
Base‐Catalyzed Decarboxylative Amination of In‐situ Generated ortho‐Quinone Methides: Synthesis of Benzyl Amines
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DOI: 10.1002/ajoc.202400380
Abstract: In this paper, a direct access to benzylic amines from in‐situ generated ortho‐quinone methides (o‐QMs) and isocya‐nate/isothiocyanate via decarboxylation is described. This base‐catalyzed methodology has high functional group tolerance and shows a wide range of… read more here.
Keywords: situ generated; ortho quinone; quinone methides; base catalyzed ... See more keywords
Photoinduced Functionalization of p‐/o‐Quinone Methides
Sign Up to like & getrecommendations! Published in 2025 at "Asian Journal of Organic Chemistry"
DOI: 10.1002/ajoc.202500516
Abstract: Quinone methides (QMs) are highly reactive intermediates and important building blocks for diverse molecular scaffolds. In recent years, there has been remarkable growth in the area of quinone methide photochemistry. Under photoirradiation conditions, p‐quinone methides… read more here.
Keywords: photoinduced functionalization; functionalization quinone; quinone methides; quinone ... See more keywords
Halogen Bond Assisted Light Responsiveness of Para‐Quinone Methides for 1,6‐Conjugate Addition Reactions
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DOI: 10.1002/cctc.202401087
Abstract: The ability to change the essential characteristics of the molecular systems using light is highly promising and finds use in photocatalysis and materials chemistry. A critical requirement for such systems is that molecules should directly… read more here.
Keywords: para quinone; visible light; halogen bond; quinone methides ... See more keywords
Phosphine‐Catalyzed 1,6‐Addition and Tandem Addition/Self‐Aldol Condensation Reactions of para‐Quinone Methides with Thiols
Sign Up to like & getrecommendations! Published in 2024 at "European Journal of Organic Chemistry"
DOI: 10.1002/ejoc.202400130
Abstract: Phosphine‐catalyzed chemodivergent reactions of para‐quinone methides (p‐QMs) affording a wide variety of diarylmethyl thioether derivatives have been reported. In the transformation presented in this work, P(4‐FC6H4)3 catalyzed the direct 1,6‐addition of p‐QMs with thiols, whereas… read more here.
Keywords: para quinone; quinone methides; addition; tandem addition ... 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
Synthesis of symmetrical chromeno[2,3-b]chromenes on the basis of о-quinone methides and 1,1-bis(morpholino)ethene
Sign Up to like & getrecommendations! Published in 2017 at "Chemistry of Heterocyclic Compounds"
DOI: 10.1007/s10593-018-2211-4
Abstract: The reaction of 1,1-bis(morpholino)ethene with precursors of о-quinone methides derived from Mannich bases of phenols and 2-naphthols provided a series of chromeno[2,3-b]chromenes. The cascade process included a hetero-Diels–Alder reaction between о-quinone methide and ketenaminal, elimination… read more here.
Keywords: quinone methides; quinone; morpholino ethene; bis morpholino ... See more keywords
1,6-Aza-Michael addition of para-quinone methides with N-heterocycles catalyzed by Zn(OTf)2: A regioselective approach to N-diarylmethyl-substituted heterocycles
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DOI: 10.1016/j.tet.2020.131338
Abstract: Abstract An efficient Zn(OTf)2-catalyzed regioselective C–N bond making reaction between a bunch of aryl/heteroaryl-substituted para-quinone methides as ideal 1,6-acceptors and various aromatic/non-aromatic aza-heterocycles bearing N–H moiety namely carbazoles, pyrazoles, indazole, benzotriazole and saccharin is reported.… read more here.
Keywords: quinone methides; michael addition; para quinone; diarylmethyl substituted ... See more keywords
1,6-Conjugate sulfonylation of para-quinone methides: An expedient approach to unsymmetrical gem-diarylmethyl sulfones
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DOI: 10.1016/j.tetlet.2018.12.023
Abstract: Abstract A novel sulfonylation of para -quinone methides with sodium arylsulfinates has been developed via acetic acid promoted sulfa-Michael addition. This reaction provides an inexpensive and efficient method to synthesize various unsymmetrical diarylmethyl sulfones, displaying… read more here.
Keywords: sulfonylation para; para quinone; quinone methides; diarylmethyl sulfones ... See more keywords
Lignin-Biosynthetic Study: Reactivity of Quinone Methides in the Diastereopreferential Formation of p-Hydroxyphenyl- and Guaiacyl-Type β- O-4 Structures.
Sign Up to like & getrecommendations! Published in 2019 at "Journal of agricultural and food chemistry"
DOI: 10.1021/acs.jafc.8b06465
Abstract: p-Quinone methides are involved in lignin biosynthesis as transient intermediates, and the aromatization step has a great impact on the chemical structure of the resulting lignin. A series of quinone methides (QMs) were synthesized and… read more here.
Keywords: qms; quinone methides; type qms; formation hydroxyphenyl ... See more keywords
Harnessing ortho-Quinone Methides in Natural Product Biosynthesis and Biocatalysis.
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DOI: 10.1021/acs.jnatprod.1c01026
Abstract: The implementation of ortho-quinone methide (o-QM) intermediates in complex molecule assembly represents a remarkably efficient strategy designed by Nature and utilized by synthetic chemists. o-QMs have been taken advantage of in biomimetic syntheses for decades,… read more here.
Keywords: quinone methides; harnessing ortho; methides natural; product ... See more keywords