A review of the syntheses of (thio)flavones, 4‐quinolones, (thio)aurones, and azaaurones from 2′‐substituted alkynones. (14th October 2021)

• Record Type: Journal Article
• Authors: In Lee, Jae
• Is Part Of: Bulletin of the Korean Chemical Society. Volume 42:Number 12(2021)
• Page Start: 1610
• Page End: 1623
• Publication Date: 2021-10-14
• Subjects: 1, 4‐addition -- alkynones -- carbonylative coupling -- 6‐endo/5‐exo cyclization -- substitution; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/bkcs.12412
• Languages: English
• ISSNs: 0253-2964

Abstract

Abstract: Flavones have been prepared by the 6‐ endo cyclization of o ‐alkynoylphenols, cyclization/deprotection of 2′‐protected alkynones, or carbonylative coupling of 2‐halophenols with arylacetylenes and subsequent cyclization. ( Z )‐Aurones have been prepared by the 5‐ exo cyclization of o ‐alkynoylphenols or oxidation of ( Z )‐benzylidenebenzofuran‐3‐ols with MnO2 . Thioflavones have been prepared by deprotection/6‐ endo cyclization of S ‐protected alkynones or by the addition of sulfur to 2′‐halo(methoxy)alkynones and subsequent cyclization. Deprotection and 5‐ exo cyclization of S ‐benzylated alkynones using HCOOH afforded ( Z )‐thioaurones. 2‐Phenyl‐4‐quinolones have been prepared by the 6‐ endo cyclization of 2′‐aminoalkynones or by the addition of amines to 2′‐haloalkynones and subsequent cyclization. Furthermore, the treatment of 2′‐aminoalkynones with triphenylphosphine afforded ( Z )‐azaaurones by 5‐ exo cyclization. Abstract : Synthetic utilization of 2′‐substituted alkynones.