The aminomethylation of hydroxylated isoflavones with 2-aminoethanol, 3-amino-1-propanol, 4-amino-1-butanol, and 5-amino-1-pentanol in the presence of excess formaldehyde led principally to 9-(2-hydroalkyl)-9,10-dihydro-4H,8H-chromeno[8,7-e][1,3]-oxazin-4-ones 4 and/or the tautomeric 7-hydroxy-8-(1,3-oxazepan-3-ylmethyl)-4H-chromen-4-ones 5. The ratio of these tautomers was dependent on solvent polarity, electronic effects of aryl substituents in the isoflavone and the structure of the amino alcohol. NMR studies confirmed the interconversion of tautomeric forms.
The aminomethylation of hydroxylated isoflavones with n class="Chemical">2-aminoethanol, 3-amino-1-propanol, 4-amino-1-butanol, and 5-amino-1-pentanol in the presence of excess formaldehyde led principally to 9-(2-hydroalkyl)-9,10-dihydro-4H,8H-chromeno[8,7-e][1,3]-oxazin-4-ones 4 and/or the tautomeric 7-hydroxy-8-(1,3-oxazepan-3-ylmethyl)-4H-chromen-4-ones 5. The ratio of these tautomers was dependent on solvent polarity, electronic effects of aryl substituents in the isoflavone and the structure of the amino alcohol. NMR studies confirmed the interconversion of tautomeric forms.
Authors: Antonina V Popova; Mykhaylo S Frasinyuk; Svitlana P Bondarenko; Wen Zhang; Yanqi Xie; Zachary M Martin; Xianfeng Cai; Michael V Fiandalo; James L Mohler; Chunming Liu; David S Watt; Vitaliy M Sviripa Journal: Chem Zvesti Date: 2018-04-28 Impact factor: 2.146
Authors: Mykhaylo S Frasinyuk; Galyna P Mrug; Svitlana P Bondarenko; Vitaliy M Sviripa; Wen Zhang; Xianfeng Cai; Michael V Fiandalo; James L Mohler; Chunming Liu; David S Watt Journal: Org Biomol Chem Date: 2015-09-29 Impact factor: 3.876
Authors: Diana Ortiz; W Armand Guiguemde; Jared T Hammill; Angela K Carrillo; Yizhe Chen; Michele Connelly; Kayla Stalheim; Carolyn Elya; Alex Johnson; Jaeki Min; Anang Shelat; David C Smithson; Lei Yang; Fangyi Zhu; R Kiplin Guy; Scott M Landfear Journal: PLoS Negl Trop Dis Date: 2017-12-29