title: Lewis acid promoted construction of chromen-4-one and isoflavone scaffolds via regio- and chemoselective domino Friedel-Crafts acylation/Allan-Robinson reaction.
abstract: A facile and efficient synthesis of chromen-4-one and isoflavone frameworks is achieved by the domino C-acylation/O-acylation/aldolization sequence. This operationally simple one-pot elegant strategy provides structurally unique chromen-4-ones and isoflavones directly from phenols via concomitant formation of multiple C-C and C-O bonds in a single operation. The outcomes of the buttressing effect, substituent dependence, and catalyst and solvent specificity during the course of the Friedel-Crafts acylation reactions are demonstrated and supported by fitting experiments.
authors.affiliation: Department of Chemistry, Faculty of Science, Banaras Hindu University, Varanasi-221005, India. mssinghbhu@yahoo.co.in.
authors.forename: Tanmoy
authors.initials: T
authors.lastname: Chanda
authors.forename: Sushobhan
authors.initials: S
authors.lastname: Chowdhury
authors.forename: Suvajit
authors.initials: S
authors.lastname: Koley
authors.forename: Namrata
authors.initials: N
authors.lastname: Anand
authors.forename: Maya Shankar
authors.initials: MS
authors.lastname: Singh
mesh_terms: D000215:Acylation; D002867:Chromones / Q000138:chemical synthesis* / Q000737:chemistry; D007529:Isoflavones / Q000138:chemical synthesis* / Q000737:chemistry; D058116:Lewis Acids / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D002867:Chromones; D007529:Isoflavones; D058116:Lewis Acids; D012997:Solvents