Four‐Component Strain‐Release‐Driven Synthesis of Functionalized Azetidines
نویسندگان
چکیده
Despite the favorable properties that azetidine rings can engender on drug-compounds, methods for diversity-oriented synthesis of azetidine-based structures are significantly underdeveloped. Herein, we report successful realization a multicomponent [1,2]-Brook rearrangement/strain-release-driven anion relay sequence and its application to modular substituted azetidines. The rapidity reaction, as confirmed by in situ infra-red spectroscopy, leverages strain-release ring-opening azabicyclo[1.1.0]butane drive equilibrium Brook rearrangement. three electrophilic coupling partners, added sequentially azabicyclo[1.1.0]butyl-lithium, could be individually varied access diverse compound library. utility this methodology was demonstrated 4-step EP2 receptor antagonist PF-04418948.
منابع مشابه
A general, enantioselective synthesis of N-alkyl terminal aziridines and C2-functionalized azetidines via organocatalysis.
A short, high-yielding protocol involving the enantioselective α-chlorination of aldehydes has been developed for the enantioselective synthesis of C2-functionalized aziridines and N-alkyl terminal azetidines from a common intermediate. This methodology allows for the rapid preparation of functionalized aziridines in 50-73% overall yields and 88-94% ee, and azetidines in 22-32% overall yields a...
متن کاملSynthesis of Functionalized Coumarins
The synthesis of functionalized 2-oxo-2H-coumarin derivatives has been studied by a one-pot reaction of o-hydroxybenzaldehyde, ethyl 2-bromoacetate and triphenylphosphine in the presence of catalytic amount of triethyl amine in EtOAc, water or under solvent free conditions. We have found the best results obtained under solvent free condition.
متن کاملsynthesis of functionalized coumarins
the synthesis of functionalized 2-oxo-2h-coumarin derivatives has been studied by a one-pot reaction of o-hydroxybenzaldehyde, ethyl 2-bromoacetate and triphenylphosphine in the presence of catalytic amount of triethyl amine in etoac, water or under solvent free conditions. we have found the best results obtained under solvent free condition.
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ژورنال
عنوان ژورنال: Angewandte Chemie
سال: 2022
ISSN: ['1521-3773', '1433-7851', '0570-0833']
DOI: https://doi.org/10.1002/ange.202214049