Selective Cu-Catalyzed Intramolecular Annulation of 3-Aryl/Heteryl-2-(diazoacetyl)-1 H-pyrroles: Synthesis of Benzo/Furo/Thieno[ e]-Fused 1 H-Indol-7-oles and Their Transformations
Publication type: Journal Article
Publication date: 2019-07-16
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
31309836
Organic Chemistry
Abstract
The Co(III)-catalyzed reaction of 1,3-dicarbonyl compounds with 2-(diazoacetyl)-2H-azirines, prepared by a simplified procedure from 2H-azirin-2-carbonyl chlorides, led in high yield to the formation of 2-(diazoacetyl)pyrroles while leaving the diazoacetyl function intact. The intramolecular aromatic substitution reaction of 2-(diazoacetyl)pyrroles, catalyzed by Cu(OTf)2, provided selectively previously unknown benzo[e]- and hetero[e]-fused indol-7-oles in good yields. Formylation of benzo[e]indol-4-ol led selectively to the 5-formyl derivative, which is a good precursor for an unusual salen ligand and its Ni-complex. Triflates prepared from benzo[e]indol-4-oles gave various 4-substituted benzo[e]indoles carrying aryl, 2-thienyl, 2-pyridyl and alkynyl groups, in excellent yields using cross-coupling reactions. 4-(2-Pyridyl)benzo[e]indoles, upon treatment with BF3·Et2O/Et3N, afforded a new type of fluorescent boron complexes with large Stokes shifts.
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Total citations:
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Citations from 2024:
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(33.33%)
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Bodunov V. A. et al. Selective Cu-Catalyzed Intramolecular Annulation of 3-Aryl/Heteryl-2-(diazoacetyl)-1 H-pyrroles: Synthesis of Benzo/Furo/Thieno[ e]-Fused 1 H-Indol-7-oles and Their Transformations // Journal of Organic Chemistry. 2019. Vol. 84. No. 16. pp. 10388-10401.
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Bodunov V. A., Galenko E. E., Sakharov P. A., Novikov M. S., Khlebnikov A. F. Selective Cu-Catalyzed Intramolecular Annulation of 3-Aryl/Heteryl-2-(diazoacetyl)-1 H-pyrroles: Synthesis of Benzo/Furo/Thieno[ e]-Fused 1 H-Indol-7-oles and Their Transformations // Journal of Organic Chemistry. 2019. Vol. 84. No. 16. pp. 10388-10401.
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TY - JOUR
DO - 10.1021/acs.joc.9b01573
UR - https://pubs.acs.org/doi/10.1021/acs.joc.9b01573
TI - Selective Cu-Catalyzed Intramolecular Annulation of 3-Aryl/Heteryl-2-(diazoacetyl)-1 H-pyrroles: Synthesis of Benzo/Furo/Thieno[ e]-Fused 1 H-Indol-7-oles and Their Transformations
T2 - Journal of Organic Chemistry
AU - Bodunov, Vladimir A
AU - Galenko, Ekaterina E
AU - Sakharov, Pavel A
AU - Novikov, Mikhail S.
AU - Khlebnikov, Alexander F
PY - 2019
DA - 2019/07/16
PB - American Chemical Society (ACS)
SP - 10388-10401
IS - 16
VL - 84
PMID - 31309836
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (up to 50 authors)
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@article{2019_Bodunov,
author = {Vladimir A Bodunov and Ekaterina E Galenko and Pavel A Sakharov and Mikhail S. Novikov and Alexander F Khlebnikov},
title = {Selective Cu-Catalyzed Intramolecular Annulation of 3-Aryl/Heteryl-2-(diazoacetyl)-1 H-pyrroles: Synthesis of Benzo/Furo/Thieno[ e]-Fused 1 H-Indol-7-oles and Their Transformations},
journal = {Journal of Organic Chemistry},
year = {2019},
volume = {84},
publisher = {American Chemical Society (ACS)},
month = {jul},
url = {https://pubs.acs.org/doi/10.1021/acs.joc.9b01573},
number = {16},
pages = {10388--10401},
doi = {10.1021/acs.joc.9b01573}
}
Cite this
MLA
Copy
Bodunov, Vladimir A., et al. “Selective Cu-Catalyzed Intramolecular Annulation of 3-Aryl/Heteryl-2-(diazoacetyl)-1 H-pyrroles: Synthesis of Benzo/Furo/Thieno[ e]-Fused 1 H-Indol-7-oles and Their Transformations.” Journal of Organic Chemistry, vol. 84, no. 16, Jul. 2019, pp. 10388-10401. https://pubs.acs.org/doi/10.1021/acs.joc.9b01573.