Imidazolyl derivatives of the chroman ring. 1

Abstract

The synthesis of 2‐(1H‐imidazol‐1‐yl)‐2,3‐dihydro‐2H‐1‐benzopyran‐4‐ones (I) through 3‐bromo‐2,3‐dihydro‐4H‐1‐benzopyran‐4‐ones or more conveniently through chroman ring closure from 2‐(1H‐imidazol‐1‐yl)‐2′‐hydroxyacetophenones is described. The ring closure also works well for the pyrazolyl derivatives. Compounds I and the corresponding imidazolylchromanols, ‐chromenes, and ‐chromans derived from the former, were pharmacologically investigated.

Chemical modifications and transformations of 3-azahetarylchroman-4-ones

“…Some of them show interesting activities both in vitro and in vivo [5]. Thus chroman-4-one 3 (R=6-Cl) and the corresponding chroman-4-ol 4 showed significant hypolipidemic activity in normolipemic rats.…”

“…Alkyl and benzyl ethers 5 can be considered as cyclic analogues of antifungal agents such as miconazole and isosters of the 2-(1H-imidazol-1-yl)-1-benzyloxytetralines (Scheme 2). The latest were active in vitro against Gram-positive bacteria, Candida albicans and dermatophytes [5].…”

“…3-(1-Imidazolyl)-2,3-dihydro-4H-1-benzopyran derivatives of the following general formula 8, have been patented (Figure 2), as well as method of preparation, pharmaceutical compositions and method of using such FRENCH-UKRAINIAN JOURNAL OF CHEMISTRY (2016, VOLUME 04, ISSUE 02) compounds to inhibit blood platelet aggregation, to increase total serum HDL cholesterol, to increase the ratio between α-lipoprotein and β-lipoprotein total cholesterol, and/or reducing total serum cholesterol or serum triglycerides [7]. n-hexane at temperature ranging from about -60° C to about -80° C (for RLi) or in anhydrous diethyl ether at temperature ranging from about 0° C to room temperature (RMgHal) [7].…”

“…n-hexane at temperature ranging from about -60° C to about -80° C (for RLi) or in anhydrous diethyl ether at temperature ranging from about 0° C to room temperature (RMgHal) [7]. Ref?…”

Stereoselective Synthesis and in Vitro Antifungal Evaluation of (E)- and (Z)-Imidazolylchromanone Oxime Ethers

“…2,3-Dihydro-3-(1H-imidazol-1-yl)-4H-1-benzopyran-4-ones 5 were obtained from 2-(1H-imidazol-1-yl)-2Ј-hydroxyacetophenones 4 according to a method reported in the literature [13]. Compounds 5 were converted to the pure (Z )-oxime derivatives (Z )-6 by stirring with 3 equiv.…”