Investigation on the thio-Claisen rearrangement of 2-[(4-aryloxy-2- butynyl)sulfanyl]thiophene
Journal Title: International Journal of Experimental Research and Review - Year 2022, Vol 27, Issue 1
Abstract
2H-thiopyrano[3,2-c]coumarins have been regioselectively produced in 55-78%yield by the thermal [3,3] sigmatropic rearrangement led us to conduct research on the thioClaisen rearrangement of 2-[(4-aryloxy-2-butynyl)sulfanyl]thiophene. Six different casesusing various 4-chlorobut-2-ynes were subjected to [3,3] sigmatropic rearrangement. Thefirst cyclization in every cases were successful. The products formed contain allyl aryl ethermoiety and as such there was scope for the second Claisen rearrangement with the products. The first Claisen product with Ar = 3,5-Me2C6H3 has been successfully undergone doubleClaisen rearrangement. As double Claisen rearrangement requires higher activation energy,the selection of solvent and catalyst was very important. In this case, anhydrous AlCl3, BF3-etherate was successfully chosen to get the reaction completed within one hour with en-hanced yield.
Authors and Affiliations
Debabrata Singha; Anwesha Bhattacharya, Nilasish Pal
Keywords
Related Articles
- EP ID EP703275
- DOI https://doi.org/10.52756/ijerr.2022.v27.006
- Views 84
- Downloads 0
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