FeCl3-Promoted Annulation of 2-Haloindoles: Switchable Synthesis of Spirooxindole-chromeno[2,3-b]indoles and Spirooxindole-chromeno[3,2-b]indoles
3
Ammoxidation Business Unit Shanghai R&D Center, Anshan Hifichem Company, Ltd., Shanghai 201100, China
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Publication type: Journal Article
Publication date: 2020-02-04
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
32013432
Organic Chemistry
Abstract
Electrophilic indoles bearing a leaving group at C2 undergo C3-regioselective dearomative hydroaryloxylation and subsequent 1,2-tertiary alkyl migration/aromatization. This is the first ring-opening migration of the spiroindolenine intermediate formed by the C3 nucleophilic addition reaction. Various spiro-oxindole-chromeno[3,2-b]/[2,3-b]indoles were successfully synthesized in excellent yields (up to 98%). This reaction features selective ring-opening migration (C-C/C-O) of the tertiary alkyl group from the indole C3 position to the C2 position stereoselectively, providing a unique synthetic method for constructing novel polycyclic indole skeletons.
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16
Total citations:
16
Citations from 2025:
2
(12.5%)
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Luo M. P. et al. FeCl3-Promoted Annulation of 2-Haloindoles: Switchable Synthesis of Spirooxindole-chromeno[2,3-b]indoles and Spirooxindole-chromeno[3,2-b]indoles // Journal of Organic Chemistry. 2020. Vol. 85. No. 5. pp. 3638-3654.
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Luo M. P., Zhu X., Liu R., Yu S., Wei W. FeCl3-Promoted Annulation of 2-Haloindoles: Switchable Synthesis of Spirooxindole-chromeno[2,3-b]indoles and Spirooxindole-chromeno[3,2-b]indoles // Journal of Organic Chemistry. 2020. Vol. 85. No. 5. pp. 3638-3654.
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TY - JOUR
DO - 10.1021/acs.joc.9b03300
UR - https://doi.org/10.1021/acs.joc.9b03300
TI - FeCl3-Promoted Annulation of 2-Haloindoles: Switchable Synthesis of Spirooxindole-chromeno[2,3-b]indoles and Spirooxindole-chromeno[3,2-b]indoles
T2 - Journal of Organic Chemistry
AU - Luo, Mu Peng
AU - Zhu, Xinlei
AU - Liu, Rufeng
AU - Yu, Shunming
AU - Wei, Wan-Guo
PY - 2020
DA - 2020/02/04
PB - American Chemical Society (ACS)
SP - 3638-3654
IS - 5
VL - 85
PMID - 32013432
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
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@article{2020_Luo,
author = {Mu Peng Luo and Xinlei Zhu and Rufeng Liu and Shunming Yu and Wan-Guo Wei},
title = {FeCl3-Promoted Annulation of 2-Haloindoles: Switchable Synthesis of Spirooxindole-chromeno[2,3-b]indoles and Spirooxindole-chromeno[3,2-b]indoles},
journal = {Journal of Organic Chemistry},
year = {2020},
volume = {85},
publisher = {American Chemical Society (ACS)},
month = {feb},
url = {https://doi.org/10.1021/acs.joc.9b03300},
number = {5},
pages = {3638--3654},
doi = {10.1021/acs.joc.9b03300}
}
Cite this
MLA
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Luo, Mu Peng, et al. “FeCl3-Promoted Annulation of 2-Haloindoles: Switchable Synthesis of Spirooxindole-chromeno[2,3-b]indoles and Spirooxindole-chromeno[3,2-b]indoles.” Journal of Organic Chemistry, vol. 85, no. 5, Feb. 2020, pp. 3638-3654. https://doi.org/10.1021/acs.joc.9b03300.