Direct approach to multi-substituted pyrroles from 2-propynylamine and 1,3-diketone or β-keto ester using Bi(OTf) 3 catalyst

Chemistry Letters

Volumn 38, Issue 3, 2009, Pages 224-225

  Komeyama, Kimihiro ^a   Miyagi, Motoyoshi ^a   Takaki, Ken ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 67650495848     PISSN: 03667022     EISSN: 13480715     Source Type: Journal    
DOI: 10.1246/cl.2009.224     Document Type: Article

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35. 3: 2, 4-Pentanedione (2a) (51.5 mg, 0.51 mmol) was added to a solution of N-tosyl-2-propynylamine (la) (52.4 mg, 0.25 mmol) and Bi (OTf) 3 (16mg, 24μmol, 10mol %) in anhydrous toluene (0.5 mL), and the reaction vial was sealed. After stirring at 100°C for 9h, the mixture was cooled to ambient temperature, passed through a short silica-gel column, and concentrated to leave the reddish black residue. Purification of the residue by column chromatography on silica gel (hexane/ethyl acetate=20/1) gave pyrroles 3a and 4a as a yellow solid (Mp. : 85.0-86.0 °C, 20 mg, 27%) and a yellow oil (29 mg, 47%), respectively.
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38. Supporting Information is available electronically on the CSJ-Journal Web site, http://www.csj.jp/journals/chem-lett/index.html.