Convenient Synthesis of Dihydrobenzofuran‐Fused Spirocyclopentane‐1,2‐Diindolinone Scaffolds
Year: 2024
Type: article
Abstract: The diverse functionalized dihydrobenzofuran‐fused spirocyclopentane‐1,2‐diindolin‐one scaffolds were conveniently synthesized by base promoted domino cyclization reaction of MBH (Morita‐Baylis‐Hillmann) carbonates of isatins and 3‐(o‐hydroxybenzylidene)indolin‐2‐ones. The base promoted reactions of MBH maleimides of isatins and MBH formates of isatins with 3‐(o‐hydroxybenzylidene)indolin‐2‐ones afforded polycyclic dispiro[indoline‐3,4′‐benzofuro[2′,3′:1,5]cyclopenta[1,2‐c]pyrrole‐5′,3′′‐indolines] and dispiro[indoline‐3,1′‐cyclopenta[b]benzofuran‐2′,3′′‐indolines] in good yields and with high diastereoselectivity. More importantly, DMAP facilitated annulation reaction of MBH nitriles of isatins and 3‐(o‐hydroxybenzylidene)indolin‐2‐ones selectively resulted in dispiro[indoline‐3,1′‐cyclopentane‐2′,3′′‐indolines], while Cs2CO3 promoted reaction gave dispiro[indoline‐3,1′‐cyclopenta[b]benzofuran‐2′,3′′‐indolines] in high yields and with high diastereoselectivity. The relative configurations of the various polycyclic compounds were clearly elucidated by determination several single crystal structures.
Authors: Ting Tang, Ying Han, Chao‐Guo Yan, Kun Huang, Jing Sun
Institution: Yangzhou University
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: bronze
Award: 准[1]轮烷和[1]轮烷的调控组装与刺激相应性能研究
OpenAlex ID: W4403485218