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A Thioannulation Approach to Substituted Thiophenes from Morita-Baylis-Hillman Acetates of Acetylenic Aldehydes

Chada Raji Reddy*, Reddi Rani Valleti and Motatipally Damoder Reddy

*Division of Natural Products Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad-500007, India, Email:

C. R. Reddy, R. R. Valleti, N. D. Reddy, J. Org. Chem., 2013, 78, 6495-6502.

DOI: 10.1021/jo400567h


A mild, metal-free and base-promoted thioannulation of Morita-Baylis-Hillman acetates of acetylenic aldehydes with potassium thioacetate to yield substituted thiophenes involves a tandem allylic substitution/deacetylative 5-exo-dig-thiocycloisomerization. The obtained products provide an entry to 4H-thieno[3,2-c]chromene and thieno[3,2-c]dihydroquinoline.

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ID: J42-Y2013