Facile Regioselective Synthesis of Benzofuran-Annulated Six-Membered Sulfur Heterocycles and the Occurrence of Thermal [1,3] Sigmatropic Rearrangement

Krishna      C. Majumdar; Sanjay      Nath; Buddhadeb      Chattopadhyay; Krishanu      Ray

doi:10.2174/157017811795038368

Abstract

Thio-Claisen rearrangement of a number of 3-(4-aryloxybut-2 – ynlthio)benzofurans has been achieved under very mild conditions to give 2H-benzo[b]thiopyrano[2,3-d]furans. Attempts at further thio-claisen rearrangement resulted in the occurrence of thermal [1s, 3a] sigmatropic shift.

Keywords: Thio-Claisen rearrangement, [3,3] sigmatropic rearrangement, sulfur heterocycles, regioselective cyclization, [1,3] hydrogen shift, thiopyrano, thieno[3,2-c]coumarins, methyl, pyranothiopyran, furan

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Letters in Organic Chemistry

Title: Facile Regioselective Synthesis of Benzofuran-Annulated Six-Membered Sulfur Heterocycles and the Occurrence of Thermal [1,3] Sigmatropic Rearrangement

Volume: 8 Issue: 3

Author(s): Krishna C. Majumdar, Sanjay Nath, Buddhadeb Chattopadhyay and Krishanu Ray

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Abstract: Thio-Claisen rearrangement of a number of 3-(4-aryloxybut-2 – ynlthio)benzofurans has been achieved under very mild conditions to give 2H-benzo[b]thiopyrano[2,3-d]furans. Attempts at further thio-claisen rearrangement resulted in the occurrence of thermal [1s, 3a] sigmatropic shift.

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C. Majumdar Krishna, Nath Sanjay, Chattopadhyay Buddhadeb and Ray Krishanu, Facile Regioselective Synthesis of Benzofuran-Annulated Six-Membered Sulfur Heterocycles and the Occurrence of Thermal [1,3] Sigmatropic Rearrangement, Letters in Organic Chemistry 2011; 8 (3) . https://dx.doi.org/10.2174/157017811795038368