Prins‐Driven Friedel–Crafts Reaction for the Stereoselective Synthesis of Hexahydroindeno[2,1‐c]pyran Derivatives

Abstract

A strategy has been devised for the stereoselective synthesis of hexahydroindeno[2,1‐c]pyran scaffolds through a domino cyclization of (E)‐3,5‐diphenylpent‐4‐en‐1‐ol with aldehydes using BF3⋅OEt2 at 70 °C. It is an approach for the construction of the indeno[2,1‐c]pyran skeleton in a one‐pot operation through a cascade cyclization.

MWW-type zeolite nanostructures for a one-pot three-component Prins–Friedel–Crafts reaction

“…12–15 This reaction involves Prins cyclization via interaction of a carbonyl compound and a homoallylic alcohol with the formation of an oxocarbenium ion that undergoes an intramolecular π-bond attack to construct a new carbon–carbon bond with a subsequent Friedel–Crafts alkylation with an arene nucleophile. 12,15 As an alternative route, an acid-catalyzed intramolecular (or tandem) Prins–Friedel–Crafts reaction of a homoallylic alcohol appended to a nucleophile with a carbonyl compound also allows one to obtain 4-aryltetrahydropyrans, 16–19 but this methodology is more complex as it requires additional synthesis steps to modify the substrate molecule.…”

Access to Hexahydroindeno[2,1-c]pyran-Based Propellanes by a Domino Prins/Friedel–Crafts Cyclization

“…[24][25][26][27][28][29] For example, Reddy et al described a concise and practical synthesis of indenopyran scaffolds from (E)-3,5-diphenylpent-4-en-1-ol 3, various aldehydes and through the activation of BF3.OEt2 at 70°C (Scheme 2). 30 Scheme 2. Tandem Prins / Friedel-Crafts reaction.…”

Synthesis, Characterization and Biological Evaluation of Isoxazoles Derived from 3-Aminoacetophenone

“…Synthesis of isoxazoles: 0.002 mol of chalcone derivatives reacted with equimolar hydroxylamine hydrochloride and sodium acetate in 25 mL ethanol and refluxed for 6 h. The mixture was concentrated and poured into crushed ice and stirred well to obtain the precipitate [6][7][8][9][10]. The precipitate obtained was filtered, washed and recrystallized.…”