Concise Synthesis of Furo[2,3-b]indolines via [3,3]-Sigmatropic Rearrangement of N-Alkenyloxyindoles
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作者:
Shevlin, Michael
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Merck & Co Inc, Dept Proc Res & Dev, 126 E Lincoln Ave, Rahway, NJ 07065 USA
Univ Illinois, Dept Chem, 845 W Taylor St, Chicago, IL 60607 USAMerck & Co Inc, Dept Proc Res & Dev, 126 E Lincoln Ave, Rahway, NJ 07065 USA
Shevlin, Michael
[1
,2
]
Strotman, Neil A.
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Merck & Co Inc, Dept Proc Res & Dev, 126 E Lincoln Ave, Rahway, NJ 07065 USAMerck & Co Inc, Dept Proc Res & Dev, 126 E Lincoln Ave, Rahway, NJ 07065 USA
Strotman, Neil A.
[1
]
Anderson, Laura L.
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Univ Illinois, Dept Chem, 845 W Taylor St, Chicago, IL 60607 USAMerck & Co Inc, Dept Proc Res & Dev, 126 E Lincoln Ave, Rahway, NJ 07065 USA
Anderson, Laura L.
[2
]
机构:
[1] Merck & Co Inc, Dept Proc Res & Dev, 126 E Lincoln Ave, Rahway, NJ 07065 USA
[2] Univ Illinois, Dept Chem, 845 W Taylor St, Chicago, IL 60607 USA
A concise new synthetic route to furo[2,3-b]indolines has been developed by taking advantage of the reactivity of N-alkenyloxyindole intermediates. These compounds spontaneously undergo [3,3]-sigmatropic rearrangement followed by cyclization to form hemiaminals as single diastereomers. Tin-promoted N-hydroxyindole formation followed by conjugate addition to activated alkynes provides simple and modular access to a diverse array of N-alkenyloxyindoles and their corresponding furo[2,3-b]indolines. Microscale high-throughput experimentation was used to facilitate investigation of the scope and tolerance of this transformation and related studies on the nucleophilic aromatic substitution and rearrangement of N-hydroxyindoles with halogenated arenes have also been evaluated.
机构:
Hangzhou City Univ, Sch Med, Key Lab Novel Targets & Drug Study Neural Repair Z, Hangzhou 310015, Peoples R China
Zhejiang Univ Technol, Coll Pharmaceut Sci, Hangzhou 310014, Peoples R ChinaHangzhou City Univ, Sch Med, Key Lab Novel Targets & Drug Study Neural Repair Z, Hangzhou 310015, Peoples R China
Luo, Fang
Wang, Wei
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Chinese Acad Sci, Tianjin Inst Ind Biotechnol, Tianjin 300308, Peoples R ChinaHangzhou City Univ, Sch Med, Key Lab Novel Targets & Drug Study Neural Repair Z, Hangzhou 310015, Peoples R China
Wang, Wei
Xiang, Chaowei
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Hangzhou City Univ, Sch Med, Key Lab Novel Targets & Drug Study Neural Repair Z, Hangzhou 310015, Peoples R ChinaHangzhou City Univ, Sch Med, Key Lab Novel Targets & Drug Study Neural Repair Z, Hangzhou 310015, Peoples R China
Xiang, Chaowei
Zeng, Linghui
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Hangzhou City Univ, Sch Med, Key Lab Novel Targets & Drug Study Neural Repair Z, Hangzhou 310015, Peoples R ChinaHangzhou City Univ, Sch Med, Key Lab Novel Targets & Drug Study Neural Repair Z, Hangzhou 310015, Peoples R China
Zeng, Linghui
Zhang, Chong
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Hangzhou City Univ, Sch Med, Key Lab Novel Targets & Drug Study Neural Repair Z, Hangzhou 310015, Peoples R ChinaHangzhou City Univ, Sch Med, Key Lab Novel Targets & Drug Study Neural Repair Z, Hangzhou 310015, Peoples R China
Zhang, Chong
Zhang, Jiankang
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Hangzhou City Univ, Sch Med, Key Lab Novel Targets & Drug Study Neural Repair Z, Hangzhou 310015, Peoples R ChinaHangzhou City Univ, Sch Med, Key Lab Novel Targets & Drug Study Neural Repair Z, Hangzhou 310015, Peoples R China
Zhang, Jiankang
Zhang, Xingxian
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Zhejiang Univ Technol, Coll Pharmaceut Sci, Hangzhou 310014, Peoples R ChinaHangzhou City Univ, Sch Med, Key Lab Novel Targets & Drug Study Neural Repair Z, Hangzhou 310015, Peoples R China
Zhang, Xingxian
Shao, Jiaan
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Hangzhou City Univ, Sch Med, Key Lab Novel Targets & Drug Study Neural Repair Z, Hangzhou 310015, Peoples R ChinaHangzhou City Univ, Sch Med, Key Lab Novel Targets & Drug Study Neural Repair Z, Hangzhou 310015, Peoples R China
Shao, Jiaan
Zhu, Huajian
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Hangzhou City Univ, Sch Med, Key Lab Novel Targets & Drug Study Neural Repair Z, Hangzhou 310015, Peoples R ChinaHangzhou City Univ, Sch Med, Key Lab Novel Targets & Drug Study Neural Repair Z, Hangzhou 310015, Peoples R China