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Synthesis of 4H-indeno[1,2-b]thiophenes, 8H-indeno[2,1-b]-thiophenes and 8H-indeno[2,1-b]furans having acrylic acid unit

✍ Scribed by Ki Joon Jeon; Kee-Jung Lee

Publisher
Journal of Heterocyclic Chemistry
Year
2008
Tongue
English
Weight
315 KB
Volume
45
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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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.

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