Temperature‐Controlled Dearomative [5+1] Spiroannulation and Formal [5+2] Cyclization of Indoles with Enynones: Divergent Synthesis of Spiro‐Indolenines and Dihydrocyclohepta[b]Indolones DOI Open Access
Bin Dong, Zhiming Li, Wei Li

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 8, 2024

Abstract We developed a temperature‐controlled intermolecular dearomative [5+1] spiroannulation and [5+2] cyclization of indoles with enynones, smoothly delivering variety spiroindolenines dihydrocyclohepta[ b ]indolones under 40 °C 80 °C, respectively. A three‐step cascade reaction was also realized by using OTBS or NHBoc containing enynones in the indole identical condition. And novel valuable highly‐oriented three‐dimensional indole‐based tetracyclic scaffold produced high yields excellent diastereoselectivities. Additionally, various spiroindolines spirooxindoles were facilely through simple operations. This highly efficient domino‐reaction represents an emblematic method for preparation polycycles pathway.

Language: Английский

Dearomatization of Aromatic Compounds: A Decade Review DOI
Jianmin Chen, Wenhao Zhang, Dayun Huang

et al.

Asian Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: May 28, 2025

Abstract Dearomatization offers an efficient strategy for directly converting arenes into cyclic molecules. In this review, we discuss representative examples of dearomatization reactions through five modes: (1) radical dearomatization, (2) halofunctionalization‐dearomatization, in which three‐membered intermediates were frequently involved, (3) nucleophilic mainly about electron‐rich arenes, (4) oxidative and (5) reductive dearomatization. Compared to heteroarenes, simple benzene are more challenging participate reactions. recent years, fewer reports have focused on benzene. Heteroarenes, inherently or easily activated, tend undergo readily. This review highlights a decade progress including indoles, benzofurans, benzothiophenes, thiophenes, furans, naphthols, naphthalenes, quinolines, pyridines, nitrobenzenes, benzenes. It also analyzes their mechanisms strategies. We hope will aid future research field.

Language: Английский

Citations

0
Temperature‐Controlled Dearomative [5+1] Spiroannulation and Formal [5+2] Cyclization of Indoles with Enynones: Divergent Synthesis of Spiro‐Indolenines and Dihydrocyclohepta[b]Indolones DOI Open Access
Bin Dong, Zhiming Li, Wei Li

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 8, 2024

Abstract We developed a temperature‐controlled intermolecular dearomative [5+1] spiroannulation and [5+2] cyclization of indoles with enynones, smoothly delivering variety spiroindolenines dihydrocyclohepta[ b ]indolones under 40 °C 80 °C, respectively. A three‐step cascade reaction was also realized by using OTBS or NHBoc containing enynones in the indole identical condition. And novel valuable highly‐oriented three‐dimensional indole‐based tetracyclic scaffold produced high yields excellent diastereoselectivities. Additionally, various spiroindolines spirooxindoles were facilely through simple operations. This highly efficient domino‐reaction represents an emblematic method for preparation polycycles pathway.

Language: Английский

Citations

0