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Construction of Spiro[indene‐2,1′‐pyrrolo[2,1‐a]isoquinoline]s through a Visible‐Light‐Catalyzed Oxidative [3+2] Cycloaddition Reaction
Author(s) -
Jiang YanHong,
Sun Jing,
Sun Qiu,
Yan ChaoGuo
Publication year - 2017
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201700125
Subject(s) - chemistry , isoquinoline , cycloaddition , indene , catalysis , oxidative phosphorylation , medicinal chemistry , visible spectrum , photochemistry , organic chemistry , biochemistry , physics , optoelectronics
Abstract Under visible‐light catalysis, a domino oxidative 1,3‐dipolar cycloaddition reaction of alkyl 2‐(3,4‐dihydroisoquinolin‐2‐yl)acetate with 2‐arylideneindane‐1,3‐diones has been developed that affords functionalized spiro[indene‐2,1′‐pyrrolo[2,1‐a]isoquinoline]s in satisfactory yields and high diastereoselectivities. Depending on the electronic properties of the aryl group, similar reactions with tert ‐butyl 2‐(3,4‐dihydroisoquinolin‐2‐yl)acetate and 2‐(3,4‐dihydroisoquinolin‐2(1 H )‐yl)acetonitrile selectively gave spiro[indene‐2,1′‐pyrrolo[2,1‐a]isoquinoline]s and 3‐arylspiro[indene‐2,2′‐oxirane]‐1,3‐diones, respectively.