|
|||||
|
|
Synthesis and reactions of 1-hydroxy-9,9a-dihydro-1H-imidazo[1,2-a]indol-2-(3H)-ones |
|
| Authors: | Vytas MartynaitisRasa Steponavi?iūt?,Sonata Krik&scaron tolaityt?Joana Solovjova,Sven Mangelinckx,Norbert De KimpeWolfgang Holzer,Algirdas &Scaron a?kus |
| Affiliation: | a Department of Organic Chemistry, Kaunas University of Technology, LT-50270 Kaunas, Lithuania b Institute of Synthetic Chemistry, Kaunas University of Technology, LT-50270 Kaunas, Lithuania c Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure links 653, B-9000 Gent, Belgium d Department of Drug Synthesis, Faculty of Life Sciences, University of Vienna, Pharmaziezentrum, A-1090 Vienna, Austria |
| Abstract: | 1-Hydroxy-9,9a-dihydro-1H-imidazo[1,2-a]indol-2(3H)-ones, as a new type of azaheterocyclic hydroxamic acids, have been synthesized regioselectively from 1-carbamoylmethyl- or 1-(methoxycarbonyl)methyl-2,3,3-trimethyl-3H-indolium salts by reaction with hydroxylamine in the presence of a strong base. The alkylation and reduction with sodium borohydride of these novel heterocycles have been investigated. When treated with protic acids 1-hydroxy- or 1-alkoxy-9,9a-dihydro-1H-imidazo[1,2-a]indol-2(3H)-ones underwent ring opening of the imidazolidine to afford 1-[2-(hydroxyamino)-2-oxoethyl]-2,3,3-trimethyl-3H-indolium salts. The structural assignments are based on extensive 1H, 13C and 15N NMR spectroscopic studies and single crystal X-ray analyses. |
| Keywords: | Hydroxamic acids Indolium salts Imidazolidinones Ring opening |
| 本文献已被 ScienceDirect 等数据库收录！ | |