منابع مشابه
Simultaneous synthesis of both rings of chromenes via a benzannulation/o-quinone methide formation/electrocyclization cascade.
A new route to the chromene ring system has been developed which involves the reaction of an α,β-unsaturated Fischer carbene complex of chromium with a propargyl ether bearing an alkenyl group on the propargylic carbon. This transformation involves a cascade of reactions that begins with a benzannulation reaction and is followed by the formation of an o-quinone methide, and finally results in t...
متن کاملQuinone methide intermediates in organic photochemistry*
Quinone methides are widely encountered reactive intermediates in the chemistry of phenols and related compounds. This paper summarizes our recent progress in uncovering new and general photochemical methods for forming quinone methides of various structural types in aqueous solution. Their mechanism of formation and subsequent chemistry are also discussed. New examples of excited-state intramo...
متن کاملA bioorthogonal ligation enabled by click cycloaddition of o-quinolinone quinone methide and vinyl thioether.
There is an increasing interest in the use of bioorthogonal ligation to advance biomedical research through selective labeling of biomolecules in living systems. Accordingly, discovering new reactions to expand the toolbox of bioorthogonal chemistry is of particular interest to chemical biologists. Herein we report a new bioorthogonal ligation enabled by click hetero-Diels-Alder (HDA) cycloaddi...
متن کاملAlCl₃·6H₂O-Catalyzed Friedel-Crafts Alkylation of Indoles by the para-Quinone Methide Moiety of Celastrol.
A classical Friedel-Crafts alkylation of different indoles catalyzed by AlCl₃·6H₂O has been developed for a well-known important natural product, celastrol, resulting in a series of derivatives for further biological evaluation. The catalyst loading was reduced to 5 mol %, the reaction proceeds at ambient temperature and reaction time is only 3 h. The product yields range from 20% to 99%. A rea...
متن کاملBioactivation of tamoxifen to metabolite E quinone methide: reaction with glutathione and DNA.
Despite the beneficial effects of tamoxifen in the treatment and prevention of breast cancer, long-term usage of this popular antiestrogen has been linked to an increased risk of developing endometrial cancer in women. One of the suggested pathways leading to the potential toxicity of tamoxifen involves its oxidative metabolism to 4-hydroxytamoxifen, which may be further oxidized to an electrop...
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ژورنال
عنوان ژورنال: Journal of the American Chemical Society
سال: 2019
ISSN: 0002-7863,1520-5126
DOI: 10.1021/jacs.9b10474