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• W3039577064 abstract "In this thesis the importance of monocyclopropanated pyrroles as a valuable intermediate for the design of highly functionalized five- and six-membered nitrogen containing heterocycles has been shown. Previously, the ring-opening of rather activated exocyclic carbon-carbon bond of cyclopropanes was realized, while the cleavage of non-activated carbon-carbon bond was challenging in the area for the long time. In the first part of the thesis we put our efforts to develop the general method of desired ring expansion on cyclopropane ring system. Delightfully, highly regio- and diastereoselective palladium-catalyzed Heck cross-coupling of monocyclopropanated pyrroles with hetero/aryl halides with concurrent ring-opening of the non-activated cyclopropane bond has been realized, delivering highly functionalized dihydropyridines and pyridines. The developed general method demonstrated the wide scope of transformation between cycloadducts and various aryl and heteroaryl substrates. Despite steric hindrance the introduction of an ester or a formyl group into the 3-position of the cyclopropanated pyrrole also proceed well in cross-coupling reaction delivering highly functionalized dihydropyridines. Notable, employing enantiopure cyclopropanated pyrrole, this transformation occurred with perfect chirality transfer, in which the Heck-arylation occurs from the convex face of the bicycle. In addition, a one-pot synthesis of biaryl pyridine was realized: starting from the Heck coupling to dihydropyridine, the subsequent addition of oxidant (DDQ) to the reaction mixture resulted in desired 2-arylpyridines, which are very important pharmacophores, albeit challenging in the preparation. Pleasantly, the substitution of alcohol on cyclopropyl group, instead of classical donor-acceptor group, also provide the desired transformation, presenting the generosity of developed palladium catalyzed Heck cross-coupling method. Finally, the transformations of corresponding dihydropyridines as a suitable intermediate was demonstrated.In the second section of the thesis, the visible light mediated ring opening of α-bromoketone furnishing valuable five membered nitrogen containing pyrrolidone derivatives was demonstrated. The irradiation of α-bromoketone thorough the oxidative quenching cycle provided the fast ring-expansion, delivering ring-opening product. The trapping products were formed utilizing oxidative quenching cycle between substrate α-bromoketone and electron enriched heterocycles. The synthesized 5-substituted 3-pyrrolidin-2-one derivatives are important intermediates and highly desirable in natural product synthesis and medicinal chemistry.Visible-light-promoted catalyzed reaction between cyclopropanated pyrrole derivatives and arylsulfonyl chlorides gave rise to the construction of sulfur containing products through the simple C–S bond-formation, which was discussed in the third section of the thesis. In addition, the direct C–H arylation of cyclopropanated pyrroles with nitrobenzenediazonium tetrafluoroborate substrate in DMF was obtained, delivering arylated cyclopropane. The provided aryl and arylsulfonylated cyclopropanes can serve a as building block for further transformation to construct complex structure molecules." @default.
• W3039577064 created "2020-07-10" @default.
• W3039577064 creator A5088810498 @default.
• W3039577064 date "2020-06-29" @default.
• W3039577064 modified "2023-09-23" @default.
• W3039577064 title "Ring-opening of monocyclopropanated N-Boc-pyrroles" @default.
• W3039577064 hasPublicationYear "2020" @default.
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