Regioselective Thorpe–Ziegler Cyclization of 3-O-Alkylated Thiophenes; Access to Aminothieno[3,2-b]furans and Aminothieno[3,4-b]furans

Abstract

A two-step synthesis of polyfunctionalized aminothieno[3,2-b]furans and aminothieno[3,4-b]furans is described and discussed. It was found that O-alkylated thiophenes bearing electron-withdrawing groups in the ortho-position undergo condensation in the presence of an excess of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). Furthermore, selective condensation on an ortho-nitrile substituent in preference to ortho-ester or ortho-ketone substituents was observed.

Key words

thienofurans - thiophenes - O-alkylation - Thorpe–Ziegler - condensation

• References

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