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

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

Journal Name: Letters in Organic Chemistry

Volume 8 , Issue 3 , 2011

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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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Article Details

Year: 2011
Page: [176 - 179]
Pages: 4
DOI: 10.2174/157017811795038368
Price: $65

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