期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 84, 期 9, 页码 5564-5581出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b00505
关键词
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资金
- sao Paulo Foundation for Science (FAPESP) [2013/07600-3, 2013/10449-5, 2018/02611-3]
- Brazilian National Council for Scientific and Technological Development (CNPq) [307840/2014-0, 422880/2016-2]
- CAPES
- Fundacao de Amparo a Pesquisa do Estado de Sao Paulo (FAPESP) [13/07600-3] Funding Source: FAPESP
The cyclopenta[b]indole moiety represents a key skeletal unit in several natural and synthetic compounds that exhibit diverse biological properties. We described herein a two-step sequence for synthesizing cyclopenta[b]indoles with great structural diversity in overall yields up to 37%. The key step was a palladium-catalyzed oxidative annulation of 3-alkylindoles (Fujiwara-Moritani reaction). The obtained cyclopenta[b]indoles were used as substrates in heterogeneous hydrogenation reactions to afford new fused indolines in moderate yields. An acid-catalyzed intramolecular cyclization of three such indolines gave tetracyclic lactams in 89, 90, and 61% yields.
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