A highly efficient and facile one pot synthesis of novel 1-glycopyranosyl-4-biaryl butenone derivatives. Issue 9 (3rd May 2023)

• Record Type: Journal Article
• Authors: Kavita, ; Maikhuri, Vipin K.; Singla, Harbansh; Maity, Jyotirmoy; Prasad, Ashok K.
• Is Part Of: Synthetic communications. Volume 53:Issue 9(2023)
• Page Start: 640
• Page End: 647
• Publication Date: 2023-05-03
• Subjects: Aldol condensation -- C-glycosides -- domino reaction -- 1-glycopyranosyl-4-biaryl butenone -- Suzuki–Miyaura coupling reaction; Organic compounds -- Synthesis -- Periodicals; Chemistry, Organic; Synthesis; 547.205
• DOI: 10.1080/00397911.2023.2190461
• Languages: English
• ISSNs: 0039-7911

Abstract

Abstract: A facile and efficient methodology, comprised of a domino reaction, a Suzuki-Miyaura coupling reaction followed by an aldol condensation has been developed to synthesize novel 1-glycopyranosyl-4-biaryl butenone derivatives in a one-pot fashion. The reaction of C -glycosides 1- C -(β-D-glucosyl)propan-2-one, 1- C -(β-D-mannosyl)propan-2-one, 1- C -(β-D-galactosyl)propan-2-one, 1- C -(β-D-lactosyl)propan-2-one with 5-bromothiophene-2-carboxaldehyde or 4-bromobenzaldehyde and different boronic acids in the presence of Pd(II)-catalyst and a base in methanol at room temperature produced various chalcone type biphenyl C -glycosides in 75–85% yields. Graphical Abstract: UF0001