期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 76, 期 21, 页码 8794-8806出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo201521v
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资金
- Deutsche Forschungsgemeinschaft (DFG, Bad Godesberg) [IRTG 1143]
- Fonds der Chemischen Industrie (Frankfurt)
2,6-Diazaheptatrienyl metal compounds 6(-)K(+) are easily accessible from the corresponding dies 6 by deprotonation using KO-t-Bu as base. According to quantum chemical calculations, they are, in comparison to other isomeric species with nitrogen atoms in other positions, highly reactive intermediates, which undergo in dilute solution at 50 degrees C ring closure reactions to form 3-aminoindole derivatives 8/10. In contrast, in more concentrated solution at room temperature, the formation of 14-membered macrocyclces 13 as a result of formal dimerization is observed. The 3-aminoindole derivatives obtained in this work possess rare substitution patterns, and the macrocyclic compounds are essentially unknown. Two-fold vinylogous derivatives 7 give rise to tricyclic systems with delta-carboline backbone 12. The experimental results are interpreted using high-level DFT calculations with regard to the possible reaction mechanism and the nature of the transition state of the five-membered ring formation. The molecular structures in the solid state of all types of compounds were elucidated by X-ray diffraction.
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