Direct, selective and oxidative conversion of alcohols to xanthenes using hydrogen peroxide

کد مقاله : 1343-ICOC

نویسندگان

مهسا وفائی سورکی * دانشگاه دامغان

چکیده مقاله

Xanthene derivatives constitute an important group in organic chemistry. These compounds have valuable and useful properties and applications in industry such as metal corrosion inhibition [1] and especially in medicine such as antibacterial, antifungal, enzyme inhibition and anticancer properties [2] as well as applications in medical imaging and biological imaging diagnostics [3]. Many reagents and conditions have been used to synthesize these derivatives from aldehydes, but reports on their synthesis from alcohols are scarce [4]. However, many of these routs have disadvantages such as unavailability of reagents or catalysts, operation at high temperatures, long reaction times, etc. Therefore, finding more efficient methods for synthesizing these valuable heterocycles is of interest to organic and medicinal chemists. Here in the present study, an efficient way is described for the synthesis of xanthene derivatives from benzylic alcohols and 2-naphthol using hydrogen peroxide (30%) as a cheap and available oxidant in ionic liquid 1-methylimidazolium tetrafluoroborate [Hmim]BF4 in a one-pot and tandem manner . Benzylic alcohols can be efficiently converted to their corresponding xanthenes in this way even in the presence of some other functional groups such as epoxide, phenol, primary non-benzylic alcohol, etc. Due to tandem operation, the use of H2O2 which produces water as byproduct, excellent yields and also the use of an ionic liquid as a green solvent, this method is consistent with green chemistry principles. Easy work up and excellent chemoselectivity are considered as other advantages of this work.

کلیدواژه ها

Alcohol, Xanthene, Hydrogen peroxide, Ionic liquid, Tandem reaction

وضعیت: پذیرفته شده