108378-98-9Relevant academic research and scientific papers
Gram-Scale Synthesis of 3-Sulfonyl Flavanones
Chang, Meng-Yang,Tsai, Yu-Lin,Chang, Yu-Lun
, p. 1033 - 1043 (2020)
In this paper, an easy-operational, high-yielding method for the gram-scale synthesis of 3-sulfonyl flavanones is described by a one-pot straightforward POCl3 mediated intermolecular (5 + 1) annulation of the β-ketosulfones with an o-hydroxyaryl group (dual nucleophile) and arylaldehydes (dual electrophile) in refluxing toluene for 3 h. A plausible mechanism is proposed and discussed. This protocol provides a highly effective annulation via one carbon-oxygen (C-O) and one carbon-carbon (C-C) bond formations.
MeONH 2·hCl-Mediated α-Methylenation/Conjugate Addition of α-Sulfonylo-Hydroxyacetophenones with Methyl Sulfoxides: Route to 3-Sulfonylchroman-4-ones
Chang, Meng-Yang,Chen, Kuan-Ting
, p. 135 - 145 (2020/09/07)
A novel and efficient route for the synthesis of 3-sulfonylchroman-4-ones from α-sulfonyl o -hydroxyacetophenones with methyl sulfoxides via a MeONH 2·HCl-mediated sequential methylenation/ conjugate addition is described. Plausible reaction mechanisms are proposed and discussed. Various reaction conditions for this novel, one-pot, environmentally friendly conversion were investigated.
Conjugate addition to 3-(ptolylsulphinyl)chromone: A route to 2-substituted chromones and chiral substituted chroman-4-ones
Saengchantara, Suthiweth T.,Wallace, Timothy W.
, p. 6553 - 6564 (2007/10/02)
3-(p-Tolylsulphinyl)chromone 3a undergoes diastereoselective conjugate addition of lithium dimethylcuprate, producing a mixture of 2-methyl-3-(p-tolylsulphinyl)chroman-4-ones. Heating the mixture to 140°C gives 2-methylchromone in quantitative yield. Desulphurisation of the mixed products from (S)-3a gives (S)-2-methylchroman-4-one with 90% e.e. Chelation of the carbonyl and sulphoxide oxygens during methyl addition accounts for the diastereo selection.
Diastereoselective Conjugate Addition to 3-(p-Tolylsulphinyl)chromone: a Route to Chiral 2-Substituted Chroman-4-ones
Saengchantara, Suthiweth T.,Wallace, Timothy W.
, p. 1592 - 1595 (2007/10/02)
Conjugate addition of lithium dimethylcuprate to 3-(p-tolylsulphinyl)chromone (1) proceeds with at least 90percent diastereoselectivity, and the products from (S)-(1) can be converted into chiral 2-methylchroman-4-one (-)-(16).
