A novel and mild Rh(iii)-catalyzed C-H activation/intramolecular condensation of 1-aryl-1H-pyrazol-5-amines with cyclic 2-diazo-1,3-diketones was developed, giving access to various important benzo[f]pyrazolo[1,5-a][1,3]diazepine scaffolds through sequential C-C/C-N bond formation in a one-pot procedure under additive- and oxidant-free conditions. Furthermore, 3-([1,1'-biphenyl]-2-ylamino)-2-ethoxycyclohex-2-enones can be obtained in good yields by constructing C-O and C-N bonds through 1,1'-insertion, dehydration, and isomerization processes.
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http://dx.doi.org/10.1039/d0ob00382d | DOI Listing |
J Org Chem
June 2023
Hunan Key Laboratory of the Research and Development of Novel Pharmaceutical Preparations, Changsha Medical University, Changsha 410219, P. R. China.
A novel protocol for synthesizing -alkyl indoles from readily available -nitrosoanilines and iodonium ylides through the rhodium(III)-catalyzed C-H bond activation/intramolecular cyclization reaction has been described. This strategy employs nitroso as a traceless directing group. The transformation features powerful reactivity, tolerates various functional groups, and proceeds with moderate yields under mild reaction conditions, providing a straightforward approach to access structurally diverse and valuable -alkyl indole derivatives.
View Article and Find Full Text PDFOrg Lett
August 2021
School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou 221116, Jiangsu, China.
An efficient synthesis of indolo[2,1-]benzazepinones through rhodium-catalyzed cascade reactions of 2-arylindoles with allyl alcohols has been developed. This work expands the scope of products that are available through C-H activation/intramolecular annulation reactions of 2-arylindoles in organic synthesis.
View Article and Find Full Text PDFOrg Biomol Chem
January 2021
Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, P.R. China.
A Rh(iii)-catalyzed cascade C-H activation/intramolecular cyclization of 3-aryl-5-isoxazolones with cyclic 2-diazo-1,3-diketones was described, leading to the formation of isoxazolo[2,3-f]phenanthridine skeletons. The protocol features the simultaneous one-pot formation of two new C-C/C-N bonds and one heterocycle in moderate-to-good yields with good functional group compatibility. It is amenable to large-scale synthesis and further transformation.
View Article and Find Full Text PDFOrg Biomol Chem
April 2020
Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, P.R. China.
A novel and mild Rh(iii)-catalyzed C-H activation/intramolecular condensation of 1-aryl-1H-pyrazol-5-amines with cyclic 2-diazo-1,3-diketones was developed, giving access to various important benzo[f]pyrazolo[1,5-a][1,3]diazepine scaffolds through sequential C-C/C-N bond formation in a one-pot procedure under additive- and oxidant-free conditions. Furthermore, 3-([1,1'-biphenyl]-2-ylamino)-2-ethoxycyclohex-2-enones can be obtained in good yields by constructing C-O and C-N bonds through 1,1'-insertion, dehydration, and isomerization processes.
View Article and Find Full Text PDFOrg Lett
March 2020
Department of Chemistry, Indian Institute of Technology Patna, Bihta 801106, Bihar, India.
An expeditious approach has been developed for the synthesis of succinimide-fused unsymmetrical 9,10-dihydrophenanthrenes from simple aryl iodides and maleimides. The developed transformation, overall proceeding with high regioselectivity via a cascade approach through palladium(II)-catalyzed Micheal-type addition/C-H activation/intramolecular cross-dehydrogenative coupling (ICDC)/C-H activation, allows formation of four fundamental carbon-carbon bonds in one-pot fashion. The reactions tolerate broad functional groups and satisfy the parameters of atom and step economy.
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