Construction of Oxepino[3,2‐b]indoles via [4+3] Annulation of 2‐Ylideneoxindoles with Crotonate‐Derived Sulfur Ylides

A [4+3] annulation of 2‐ylideneoxindoles with crotonate‐derived sulfur ylides has been developed. A series of oxepino[3,2‐b]indoles were prepared in moderate to excellent yields (62‐93%) under mild conditions. Moreover, the synthetic oxepino[3,2‐b] indoles can be further transformed into more comple...

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Published inAdvanced synthesis & catalysis Vol. 363; no. 12; pp. 3018 - 3024
Main Authors Fei, Xing‐Hai, Zhao, Yong‐Long, Yang, Fen‐Fen, Guan, Xiang, Li, Zong‐Qin, Wang, Da‐Peng, Zhou, Meng, Yang, Yuan‐Yong, He, Bin
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 21.06.2021
Subjects
2-ylideneoxindoles
[4+3] annulation
Chemistry
Chemistry, Applied
Chemistry, Organic
oxepino[3,2-b]indoles
Physical Sciences
Science & Technology
sulfur ylides
DOMINO REACTION
2-ylideneoxindoles
oxepino[3,2-b]indoles
MICHAEL ADDITION
BETA-NUCLEOPHILIC SUBSTITUTION
BENZANNULATION
INHIBITION
DIASTEREOSELECTIVE SYNTHESIS
INDOLE
[4+3] annulation
CYCLIZATION REACTIONS
STEREOSELECTIVE-SYNTHESIS
sulfur ylides
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Abstract A [4+3] annulation of 2‐ylideneoxindoles with crotonate‐derived sulfur ylides has been developed. A series of oxepino[3,2‐b]indoles were prepared in moderate to excellent yields (62‐93%) under mild conditions. Moreover, the synthetic oxepino[3,2‐b] indoles can be further transformed into more complex cyclopropa[5,6]oxepino[3,2‐b]indoles via a [2+1] cyclopropanation. In addition, the synthetic compounds show certain antiproliferative activity against K562 and MCF‐7 cells, and its IC50 values for these two kinds of tumor cells up to 5.40±0.88 μM and 18.41±0.50 μM, respectively.
AbstractList A [4+3] annulation of 2-ylideneoxindoles with crotonate-derived sulfur ylides has been developed. A series of oxepino[3,2-b]indoles were prepared in moderate to excellent yields (62-93%) under mild conditions. Moreover, the synthetic oxepino[3,2-b] indoles can be further transformed into more complex cyclopropa[5,6]oxepino[3,2-b]indoles via a [2+1] cyclopropanation. In addition, the synthetic compounds show certain antiproliferative activity against K562 and MCF-7 cells, and its IC50 values for these two kinds of tumor cells up to 5.40 +/- 0.88 mu M and 18.41 +/- 0.50 mu M, respectively.
A [4+3] annulation of 2‐ylideneoxindoles with crotonate‐derived sulfur ylides has been developed. A series of oxepino[3,2‐ b ]indoles were prepared in moderate to excellent yields (62‐93%) under mild conditions. Moreover, the synthetic oxepino[3,2‐ b ] indoles can be further transformed into more complex cyclopropa[5,6]oxepino[3,2‐ b ]indoles via a [2+1] cyclopropanation. In addition, the synthetic compounds show certain antiproliferative activity against K562 and MCF‐7 cells, and its IC 50 values for these two kinds of tumor cells up to 5.40±0.88 μM and 18.41±0.50 μM, respectively. magnified image
A [4+3] annulation of 2‐ylideneoxindoles with crotonate‐derived sulfur ylides has been developed. A series of oxepino[3,2‐b]indoles were prepared in moderate to excellent yields (62‐93%) under mild conditions. Moreover, the synthetic oxepino[3,2‐b] indoles can be further transformed into more complex cyclopropa[5,6]oxepino[3,2‐b]indoles via a [2+1] cyclopropanation. In addition, the synthetic compounds show certain antiproliferative activity against K562 and MCF‐7 cells, and its IC50 values for these two kinds of tumor cells up to 5.40±0.88 μM and 18.41±0.50 μM, respectively.
Author He, Bin
Zhao, Yong‐Long
Yang, Yuan‐Yong
Fei, Xing‐Hai
Wang, Da‐Peng
Guan, Xiang
Zhou, Meng
Yang, Fen‐Fen
Li, Zong‐Qin
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Issue 12
Keywords DOMINO REACTION
2-ylideneoxindoles
oxepino[3,2-b]indoles
MICHAEL ADDITION
BETA-NUCLEOPHILIC SUBSTITUTION
BENZANNULATION
INHIBITION
DIASTEREOSELECTIVE SYNTHESIS
INDOLE
[4+3] annulation
CYCLIZATION REACTIONS
STEREOSELECTIVE-SYNTHESIS
sulfur ylides
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Snippet A [4+3] annulation of 2‐ylideneoxindoles with crotonate‐derived sulfur ylides has been developed. A series of oxepino[3,2‐b]indoles were prepared in moderate...
A [4+3] annulation of 2‐ylideneoxindoles with crotonate‐derived sulfur ylides has been developed. A series of oxepino[3,2‐ b ]indoles were prepared in moderate...
A [4+3] annulation of 2-ylideneoxindoles with crotonate-derived sulfur ylides has been developed. A series of oxepino[3,2-b]indoles were prepared in moderate...
Source Web of Science
SourceID webofscience
crossref
wiley
SourceType Enrichment Source
Index Database
Publisher
StartPage 3018
SubjectTerms 2-ylideneoxindoles
[4+3] annulation
Chemistry
Chemistry, Applied
Chemistry, Organic
oxepino[3,2-b]indoles
Physical Sciences
Science & Technology
sulfur ylides
Title Construction of Oxepino[3,2‐b]indoles via [4+3] Annulation of 2‐Ylideneoxindoles with Crotonate‐Derived Sulfur Ylides
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fadsc.202001580
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