3-Nitroindoles Serving as <i<N</i<-Centered Nucleophiles for Aza-1,6-Michael Addition to <i<para</i<-Quinone Methides
An unprecedented <i<N</i<-alkylation of 3-nitroindoles with <i<para</i<-quinone methides was developed for the first time. Using potassium carbonate as the base, a wide range of structurally diverse <i<N</i<-diarylmethylindole derivatives were obtained with moderated to good yields via the protection group migration/<i<aza</i<-1,6-Michael addition sequences. The reaction process was also demonstrated by control experiments. Different from the previous advances where 3-nitrodoles served as electrophiles trapping by various nucleophiles, the reaction herein is featured that 3-nitrodoles is defined with latent <i<N</i<-centered nucleophiles to react with <i<ortho</i<-hydrophenyl <i<p</i<-QMs for construction of various <i<N</i<-diarylmethylindoles..
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2023 |
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| Erschienen: |
2023 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:28 |
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| Enthalten in: |
Molecules - 28(2023), 14, p 5529 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Jian-Qiang Zhao [VerfasserIn] |
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| Links: |
doi.org [kostenfrei] |
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| Themen: |
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| doi: |
10.3390/molecules28145529 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
DOAJ093850387 |
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| 520 | |a An unprecedented <i<N</i<-alkylation of 3-nitroindoles with <i<para</i<-quinone methides was developed for the first time. Using potassium carbonate as the base, a wide range of structurally diverse <i<N</i<-diarylmethylindole derivatives were obtained with moderated to good yields via the protection group migration/<i<aza</i<-1,6-Michael addition sequences. The reaction process was also demonstrated by control experiments. Different from the previous advances where 3-nitrodoles served as electrophiles trapping by various nucleophiles, the reaction herein is featured that 3-nitrodoles is defined with latent <i<N</i<-centered nucleophiles to react with <i<ortho</i<-hydrophenyl <i<p</i<-QMs for construction of various <i<N</i<-diarylmethylindoles. | ||
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| 700 | 0 | |a Shun Zhou |e verfasserin |4 aut | |
| 700 | 0 | |a Qi-Lin Xiao |e verfasserin |4 aut | |
| 700 | 0 | |a Xi-Sha Xue |e verfasserin |4 aut | |
| 700 | 0 | |a Yan-Ping Zhang |e verfasserin |4 aut | |
| 700 | 0 | |a Yong You |e verfasserin |4 aut | |
| 700 | 0 | |a Zhen-Hua Wang |e verfasserin |4 aut | |
| 700 | 0 | |a Wei-Cheng Yuan |e verfasserin |4 aut | |
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