標題: | Design, synthesis and diversification of natural product-inspired hydantoin-fused tetrahydroazepino indoles |
作者: | Barve, Indrajeet J. Dalvi, Prashant B. Thikekar, Tushar Ulhas Chanda, Kaushik Liu, Yu-Li Fang, Chiu-Ping Liu, Chia-Chen Sun, Chung-Ming 應用化學系 Department of Applied Chemistry |
公開日期: | 1-一月-2015 |
摘要: | A facile and efficient synthesis of novel oxo, thio and seleno hydantoin fused tetrahydroazepino [4,5-b] indoles was reported. A naturally occurring iboga class alkaloid inspired seven-membered azepino[4,5-b] indole ring was synthesized as a new scaffold through Pictet-Spengler reaction followed by skeletal rearrangement of the aziridine ring. To improve the efficiency of the synthetic route, the double bond of the rearranged olefinic product 5 was reduced and a privileged hydantoin moiety was constructed on the core system through urea formation using a variety of isocyanates, isothiocyanates and isoselenocyanates followed by intramolecular cyclization to incorporate elements of diversity. The regeneration of the double bond of intermediate 9 afforded hydantoin-fused tetrahydroazepino [4,5-b] indoles. |
URI: | http://dx.doi.org/10.1039/c5ra12063b http://hdl.handle.net/11536/128188 |
ISSN: | 2046-2069 |
DOI: | 10.1039/c5ra12063b |
期刊: | RSC ADVANCES |
Volume: | 5 |
Issue: | 89 |
起始頁: | 73169 |
結束頁: | 73179 |
顯示於類別: | 期刊論文 |