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- Title
4‐Aryl‐1H‐isochromenes Synthesis from Triol Derivatives through Brønsted Acid‐Catalyzed Pinacol Rearrangement/Intramolecular Cyclization Sequence.
- Authors
Ieawsuwan, Winai; Limjirawatthana, Suphaporn; Ploypradith, Poonsakdi; Ruchirawat, Somsak
- Abstract
4‐Aryl‐1H‐isochromene derivatives have been successfully synthesized by Brønsted acid‐catalyzed pinacol rearrangement/intramolecular cyclization of the substituted 1‐(2‐(hydroxymethyl)phenyl)‐2‐arylethane‐1,2‐diols. The reaction generally proceeded with low catalyst loading of trifluoromethanesulfonic acid (5 mol%) for short reaction times (10‐20 min) to furnish the desired 4‐aryl‐1H‐isochromenes which were subsequently hydrogenated to 4‐aryl‐isochromans with up to 90 % yield. Moreover, oxidation of the resulting 4‐aryl‐isochroman provided the desired 4‐aryl‐isochroman‐1‐one in good yield.
- Subjects
PINACOL rearrangement; METHYL triflate; RING formation (Chemistry); GLYCOLS; BRONSTED acids; HYDROXYMETHYL compounds
- Publication
Asian Journal of Organic Chemistry, 2024, Vol 13, Issue 2, p1
- ISSN
2193-5807
- Publication type
Article
- DOI
10.1002/ajoc.202300578