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-Jan-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
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