Unprecedented Reactivity of γ‐Amino Cyclopentenone Enables Diversity‐Oriented Access to Functionalized Indoles and Indole‐Annulated Ring Structures
Publication type: Journal Article
Publication date: 2021-03-10
scimago Q1
wos Q1
SJR: 5.550
CiteScore: 27.6
Impact factor: 16.9
ISSN: 14337851, 15213773
PubMed ID:
33527571
General Chemistry
Catalysis
Abstract
Observation of an unexpected, Lewis acid promoted displacement of latent reactive I³-amino group on cyclopentenone presented unparalleled opportunity for enone functionalization and annulations with indole derivatives, which is developed in the current study. Herein, a vast range of C3/ N -indolyl enones and indole alkaloid-like compound were accessed in excellent yields (up to 99%) and selectivity through a one-pot operation. The mechanism most likely involves an unprecedented trait of Piancatelli-type rearrangement where influence of the gem -diaryl group appeared crucial.
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Metrics
27
Total citations:
27
Citations from 2024:
11
(40.74%)
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GOST
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Mondal B. et al. Unprecedented Reactivity of γ‐Amino Cyclopentenone Enables Diversity‐Oriented Access to Functionalized Indoles and Indole‐Annulated Ring Structures // Angewandte Chemie - International Edition. 2021. Vol. 60. No. 16. pp. 8808-8812.
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Mondal B., Pramanik S., Das D., Saha J. Unprecedented Reactivity of γ‐Amino Cyclopentenone Enables Diversity‐Oriented Access to Functionalized Indoles and Indole‐Annulated Ring Structures // Angewandte Chemie - International Edition. 2021. Vol. 60. No. 16. pp. 8808-8812.
Cite this
RIS
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TY - JOUR
DO - 10.1002/anie.202016015
UR - https://doi.org/10.1002/anie.202016015
TI - Unprecedented Reactivity of γ‐Amino Cyclopentenone Enables Diversity‐Oriented Access to Functionalized Indoles and Indole‐Annulated Ring Structures
T2 - Angewandte Chemie - International Edition
AU - Mondal, Biplab
AU - Pramanik, Sourav
AU - Das, Dinabandhu
AU - Saha, Jaideep
PY - 2021
DA - 2021/03/10
PB - Wiley
SP - 8808-8812
IS - 16
VL - 60
PMID - 33527571
SN - 1433-7851
SN - 1521-3773
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2021_Mondal,
author = {Biplab Mondal and Sourav Pramanik and Dinabandhu Das and Jaideep Saha},
title = {Unprecedented Reactivity of γ‐Amino Cyclopentenone Enables Diversity‐Oriented Access to Functionalized Indoles and Indole‐Annulated Ring Structures},
journal = {Angewandte Chemie - International Edition},
year = {2021},
volume = {60},
publisher = {Wiley},
month = {mar},
url = {https://doi.org/10.1002/anie.202016015},
number = {16},
pages = {8808--8812},
doi = {10.1002/anie.202016015}
}
Cite this
MLA
Copy
Mondal, Biplab, et al. “Unprecedented Reactivity of γ‐Amino Cyclopentenone Enables Diversity‐Oriented Access to Functionalized Indoles and Indole‐Annulated Ring Structures.” Angewandte Chemie - International Edition, vol. 60, no. 16, Mar. 2021, pp. 8808-8812. https://doi.org/10.1002/anie.202016015.