The chemical reactivity of naphthols and their derivatives toward α-cyanocinnamonitriles and ethyl α-cyanocinnamates: A review of synthesis, reactions and applications of naphthopyrano

Abstract

KEYWORDSThis review deals with synthesis and reactions of some naphthopyrano derivatives and their applications. The main purpose of this review is to present a survey of literatures on the reactivity of naphthols and their derivatives toward α-cyanocinnamonitrile or ethyl α-cyanocinnamate derivatives and the reactions of β-enaminonitriles and β-enaminoesters with different electrophiles followed by nucleophilic reagents. Some of these reactions have been applied successfully to the synthesis of biologically important compounds. Naphthols Naphthopyran Nucleophilic reagents α-Cyanocinnamonitrile Naphthopyranopyrimidine Naphthopyranotriazolopyrimidine

Synthesis of Functionalized Arenopyrans and Arenylsulfanes by Reacting Nitroallylic Acetates with Arenols and Arenethiols

“…Different approaches for the synthesis of arenopyrans, including naphthopyrans,, , encompass reaction of phenols with unsaturated acids and trans ‐dienes, reaction of salicylaldehyde with nitroalkenes or allyl bromides, three‐component reaction of aldehydes and malononitrile with either methyl acetoacetate or 8‐hydroxyquinoline, Brønsted acid catalysed intramolecular Friedel–Crafts alkylation of electron rich arenes with tethered epoxides, to name a few. Naphthopyran synthesis involving a Claisen rearrangement, using 2‐naphthol and diarylpropynol, has also been reported …”

Atroposelective Synthesis of Axially Chiral All‐Benzenoid Biaryls by the Gold‐Catalyzed Intramolecular Hydroarylation of Alkynones

“…As thus‐obtained biaryls 4a and 4i possess the electron‐rich 2‐phenanthrenol moiety, their electrophilic aromatic bromination was examined. [6b], Bromination of (–)‐ 4a with N ‐bromosuccinimide (NBS, 1.1 equiv.) proceeded in DMF at room temperature to give corresponding monobromide (–)‐ 5 and dibromide (–)‐ 6 in a ratio of 1:1 (Scheme ).…”

Concise Syntheses and Biological Activities of Ganomycin I and Fornicin A

“…Substituted naphthols provide a route to biologically active naphthopyrans, similar to the natural product mollugin 12. The methoxylated naphthyl compound guieranone A (isolated from the leaves of Guiera senegalensis ), has been shown to have potent antifungal activity 13.…”