期刊
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY
卷 16, 期 7, 页码 1517-1526出版社
SPRINGER
DOI: 10.1007/s13738-019-01632-3
关键词
Ugi reaction; 2-Formylindole; Multicomponent reaction; alpha,beta-Unsaturated acids; Cyclization; Intramolecular hydroamination; DFT; ECD spectra
资金
- Alzahra University
- Iran National Science Foundation (INSF)
A novel series of oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indoles were synthesized via a two-step pathway. In the first step, Ugi-four-component condensation of 2-formylindole, amines, (E)-4-alkoxy-4-oxobut-2-enoic acids, and isocyanides gave the corresponding Ugi-adducts. This adduct underwent intramolecular hydroamination in the presence of K2CO3 in CH3CN at room temperature to afford diastereoselective synthesis of a range of oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indoles. A comparison of experimentally observed CD and UV-visible spectra with the theoretical DFT calculated ECD spectra was used to predict the major diastereomer.
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