InBr3‑Mediated One-Pot Synthesis of 2‑(Polyhydroxylatedalkyl)‑N‑aryl-/-alkylpyrroles from 1,2-Cyclopropa-3-pyranone and Amines

InBr3‑Mediated One-Pot Synthesis of 2‑(Polyhydroxylatedalkyl)‑N‑aryl-/-alkylpyrroles from 1,2-Cyclopropa-3-pyranone and Amines

An efficient one-pot synthesis of polyhydroxyalkyl-substituted pyrroles from 1,2-cyclopropa-3-pyranones with primary amines is reported. With 10% of InBr3 as the catalyst, both aryl- and alkylamines as well as various 1,2-cyclopropa-3-pyranones are well tolerated. This method is highly appealing bec...

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Veröffentlicht in:Organic letters 2013-08, Vol.15 (15), p.3852-3855
Hauptverfasser: Wang, Pingyuan, Song, Shanshan, Miao, Zehong, Yang, Guangfu, Zhang, Ao
Format: Artikel
Sprache:eng
Schlagworte:
Amines - chemistry
Catalysis
Indium - chemistry
Molecular Structure
Pyrones - chemical synthesis
Pyrones - chemistry
Pyrroles - chemical synthesis
Pyrroles - chemistry
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Zusammenfassung:An efficient one-pot synthesis of polyhydroxyalkyl-substituted pyrroles from 1,2-cyclopropa-3-pyranones with primary amines is reported. With 10% of InBr3 as the catalyst, both aryl- and alkylamines as well as various 1,2-cyclopropa-3-pyranones are well tolerated. This method is highly appealing because of its one-pot process, mild reaction conditions, substrate simplicity, and broad substrate scope.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol401489x