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Hydroxyacetophenone ring closure

Adile Ayati, Mehraban Falahati, Hamid Irannejad, Saeed Emami
UNLABELLED: HASH(0x3637890) BACKGROUND: The currently available antifungal drugs suffer from toxicity, greatest potential drug interactions with other drugs, insufficient pharmacokinetics properties, and development of resistance. Thus, development of new antifungal agents with optimum pharmacokinetics and less toxicity is urgent task. In the search for new azole antifungals, we have been previously described azolylchromanone oxime ethers as rigid analogs of oxiconazole...
2012: Daru: Journal of Faculty of Pharmacy, Tehran University of Medical Sciences
Jotham W Coe, Krista E Bianco, Brian P Boscoe, Paige R Brooks, Eric D Cox, Michael G Vetelino
Oxidative ring closure of alkyl-substituted 2-hydroxyacetophenone trifluoromethanesulfonate esters (triflates) occurs upon exposure to base in anaerobic DMF at 20-90 degrees C. Alkyl substitution is required for ring closure. A migrated enol triflate product forms at lower temperature in high yield via migration of the trifluoromethanesulfonate in the unsubstituted and monoalkyl-substituted cases. The alkyl-substituted enol triflates also enter into the benzofuran-3-one ring-forming process under thermal cyclization conditions...
December 26, 2003: Journal of Organic Chemistry
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