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Single-atom skeletal editing of 2H-indazoles enabled by difluorocarbene

Science China Chemistry 2023年第7期66卷 1975-1981页

作者： Yao Zhou Fuling Chen Ziru Li Junjie Dong Jingnan Li Bohao Zhang Qiuling Song Hubei Key Laboratory of Pollutant Analysis&Reuse Technology College of Chemistry and Chemical EngineeringHubei Normal UniversityHuangshi 435002China Key Laboratory of Molecule Synthesis and Function Discovery Fujian Province UniversityCollege of Chemistry at Fuzhou University Fuzhou 350108China

A novel difluorocarbene promoted single-atom skeletal editing of 2H-indazoles is demonstrated *** bromodifluoroacetate was severed as the difluorocarbene source in the current protocol,facilitating the cleavage of the N-N bond via carbon atom *** metal-free ring expansion reaction enables the late-stage diversification of indazole skeletons,assembling a diverse array of functionalized quinazolin-4(3H)-ones in decent yields with excellent functional group compatibility.

关键词： indazoles skeletal editing difluorocarbene N-N bond cleavage quinazolin-4(3H)-ones

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Synthesis of 2H-benzo[g]furo/thieno/pyrrolo[2,3-e]indazoles via Intramolecular Dehydrogenation Photocyclization

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Chinese Journal of Chemistry 2021年第8期39卷 2213-2219页

作者： Wei Zhang Ping Wang Xi Zhang Rui Wang Tao Wang Zhicun Liu Zunting Zhang Key Laboratory of the Ministry of Education for Medicinal Resources and Natural Pharmaceutical Chemistry National Engineering Laboratory for Resource Development of Endangered Crude Drugs in Northwest of ChinaSchool of Chemistry and Chemical Engineeringand Basic Experimental Teaching CenterShaanxi Normal UniversityXi'anShaanxi 710062China

A catalyst-,acid-and base-free,environmental-friendly method for synthesis of 2/7-benzo[g]furo[2,3-e]indazoles,2H-benzo[g]-thieno[2,3-e]indazoles and 2H-benzo[g]pyrrolo[2,3-e]indazoles via UV light irradiation of 3-phenyl-4-(2-heteroaryl)pyrazoles(aryl=furanyl,thiophenyl and N-methylpyrrolyl)in EtOH/H_(2)O at room temperature under argon atmosphere was described.

关键词： indazoles 6π-electroncyclization Photocyclization Dehydrogenative annulation Chemo-selectivity

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Direct C-H Alkenylation of Functionalized indazoles under High-speed Ball-milling Conditions

Direct C-H Alkenylation of Functionalized Indazoles under Hi...

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中国化学会·第十五届全国有机合成化学学术研讨会

作者： Xinjie Yang 俞静波 Weike Su Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals Zhejiang University of Technology 浙江工业大学

Transition metal-catalyzed alkenylation of heteroarene C-H bonds has regained considerable attention over recent years .These reactions can potentially provide concise routes for constructing various drugs and drug *** an important class of heteroarenes, indazole motifs are embedded in numerous pharmaceuticals with a broad range of biological activities , including axitinib, pazopanib, benzydamine, granisetron, and ***, the installation of alkenyl groups onto the indazole ring has had limited success, particularly for(1H) indazole which confront with formidable challenge due to lack of *** two examples of alkenylation of(1H) indazole have been reported so far .However, these methods are more or less suffered from harsh reaction conditions such as noble metal oxidant, environmentally unfriendly solvent, or high ***, both their yields and substrate scope remain to be substantially ***, we developed a highly efficient and mild catalytic system for the C-3 alkenylation of(1H) indazole through C-H activation under high-speed ball-milling(HSBM) conditions with wide substrate scope and good yields.

关键词： indazoles C-H activation alkenylation ball milling

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