Formal ring-opening/cross-coupling reactions of 2-pyrones: iron-catalyzed entry into stereodefined dienyl carboxylates.
نویسندگان
چکیده
Open access: Despite the exceptional level of sophistication in cross-coupling chemistry, reactions of substrates that incorporate the leaving group as an integral part into a heterocyclic scaffold are scarce. The title reaction outlines the utility of this reaction format (see scheme; acac=acetylacetonate), provides a convenient entry into stereodefined diene carboxylates, and adds a new chapter to the field of iron catalysis.
منابع مشابه
Concise Synthesis of a Pateamine A Analogue with In Vivo Anticancer Activity Based on an Iron-Catalyzed Pyrone Ring Opening/Cross-Coupling.
The marine macrolide pateamine A and its non-natural sibling DMDA-Pat A are potent translation inhibitors targeting the eukaryotic initiation factor 4A (eIF4A), an enzyme with RNA helicase activity. Although essential for every living cell, this protein target seems "drugable" since DMDA-Pat A has previously been shown to exhibit remarkable in vivo activity against two different melanoma mouse ...
متن کاملGold(I)-Catalyzed Coupling Reactions for the Synthesis of Diverse Small Molecules Using the Build/Couple/Pair Strategy
The build/couple/pair strategy has yielded small molecules with stereochemical and skeletal diversity by using short reaction sequences. Subsequent screening has shown that these compounds can achieve biological tasks considered challenging if not impossible ('undruggable') for small molecules. We have developed gold(I)-catalyzed cascade reactions of easily prepared propargyl propiolates as a m...
متن کاملAccess to Indole-Fused Polyheterocycles via Pd-Catalyzed Base-Free Intramolecular Cross Dehydrogenative Coupling.
A base-free process to access indole-fused polyheterocycles via a highly efficient and atom-economic palladium-catalyzed intramolecular cross dehydrogenetive coupling (CDC) reaction of 4-aniline substituted coumarins, quinolinones, and pyrones has been developed. A wide range of indolo[3,2-c]coumarins, indolo[3,2-c]quinolinones, and indolo[3,2-c]pyrones can be facilely afforded in good to excel...
متن کاملGeneration of diverse 2-pyrones via palladium-catalyzed site-selective Suzuki-Miyaura couplings of 3-bromo-4-tosyloxy-2-pyrone.
Based on different reactivity of the (pseudo)halide substituents in the 2-pyrone (3-Br and 4-OTs), palladium-catalyzed sequential site-selective Suzuki-Miyaura cross-coupling reactions of 3-bromo-6-methyl-4-tosyloxy-2-pyrone are described, which afford the diverse 2-pyrones in good yields.
متن کاملSynthesis of quinoline-3-carboxylates by a Rh(II)-catalyzed cyclopropanation-ring expansion reaction of indoles with halodiazoacetates
In this letter, we report a novel synthesis of ethyl quinoline-3-carboxylates from reactions between a series of indoles and halodiazoacetates. The formation of the quinoline structure is probably the result of a cyclopropanation at the 2- and 3-positions of the indole followed by ring-opening of the cyclopropane and elimination of H-X.
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Angewandte Chemie
دوره 52 49 شماره
صفحات -
تاریخ انتشار 2013