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Synthesis of 4 H‐ indeno[1,2‐ b ]thiophenes, 8 H ‐indeno[2,1‐ b ]‐thiophenes and 8 H ‐indeno[2,1‐ b ]furans having acrylic acid unit
Author(s) -
Jeon Ki Joon,
Lee KeeJung
Publication year - 2008
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570450252
Subject(s) - chemistry , benzaldehyde , methyl acrylate , organic chemistry , medicinal chemistry , acryloyl chloride , furan , methyl iodide , sulfuric acid , chloride , hydroxymethyl , acrylate , catalysis , monomer , copolymer , polymer
Treatment of methyl propiolate and 2‐(thiophen‐2‐yl)benzaldehyde, 2‐(thiophen‐3‐yl)benzaldehyde or 2‐(furan‐3‐yl)benzaldehyde with tetrabutylammonium iodide/zirconium (IV) chloride or treatment of methyl acrylate and the same aldehydes with 1,4‐diazabicyclo[2,2,2]octane and triethanolamine induce an aldol‐type reaction to furnish Baylis‐Hillman adducts β‐iodo‐α‐(hydroxymethyl)acrylates or α‐(hydroxy‐methyl)acrylates, respectively. These can be used for the preparation of indenothiophenes and indenofurans having acrylic acid unit by intramolecular Friedel‐Crafts reaction with sulfuric acid in tetrachloromethane.