Annulation of a Highly Functionalized Diazo Building Block with Indoles under Sc(OTf)3/Rh2(OAc)4 Multicatalysis through Michael Addition/Cyclization Sequence
Publication type: Journal Article
Publication date: 2018-09-04
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
30178678
Organic Chemistry
Abstract
A highly functionalized and easily accessible six-carbon diazo building block has been developed and utilized as a 1,4-diacceptor for an efficient synthesis of functionalized tetrahydrocarbazoles, carbazoles, and tetrahydropyrido[1,2- a]indoles. The synthesis involves concurrent tandem catalysis by Sc(OTf)3 and Rh2(OAc)4. The role of Sc(OTf)3 is critical as it facilitates both the initial intermolecular Michael reaction of the indole and the subsequent Rh(II)-catalyzed intramolecular annulation. The products, tetrahydrocarbazoles and tetrahydropyridoindoles, are equipped with a β-ketoester and ester functionalities which can be utilized for further synthetic elaborations.
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Total citations:
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Citations from 2024:
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(22.73%)
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GOST
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Sakthivel S., Balamurugan R. Annulation of a Highly Functionalized Diazo Building Block with Indoles under Sc(OTf)3/Rh2(OAc)4 Multicatalysis through Michael Addition/Cyclization Sequence // Journal of Organic Chemistry. 2018. Vol. 83. No. 19. pp. 12171-12183.
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Sakthivel S., Balamurugan R. Annulation of a Highly Functionalized Diazo Building Block with Indoles under Sc(OTf)3/Rh2(OAc)4 Multicatalysis through Michael Addition/Cyclization Sequence // Journal of Organic Chemistry. 2018. Vol. 83. No. 19. pp. 12171-12183.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.joc.8b02127
UR - https://doi.org/10.1021/acs.joc.8b02127
TI - Annulation of a Highly Functionalized Diazo Building Block with Indoles under Sc(OTf)3/Rh2(OAc)4 Multicatalysis through Michael Addition/Cyclization Sequence
T2 - Journal of Organic Chemistry
AU - Sakthivel, Shanmugam
AU - Balamurugan, Rengarajan
PY - 2018
DA - 2018/09/04
PB - American Chemical Society (ACS)
SP - 12171-12183
IS - 19
VL - 83
PMID - 30178678
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2018_Sakthivel,
author = {Shanmugam Sakthivel and Rengarajan Balamurugan},
title = {Annulation of a Highly Functionalized Diazo Building Block with Indoles under Sc(OTf)3/Rh2(OAc)4 Multicatalysis through Michael Addition/Cyclization Sequence},
journal = {Journal of Organic Chemistry},
year = {2018},
volume = {83},
publisher = {American Chemical Society (ACS)},
month = {sep},
url = {https://doi.org/10.1021/acs.joc.8b02127},
number = {19},
pages = {12171--12183},
doi = {10.1021/acs.joc.8b02127}
}
Cite this
MLA
Copy
Sakthivel, Shanmugam, and Rengarajan Balamurugan. “Annulation of a Highly Functionalized Diazo Building Block with Indoles under Sc(OTf)3/Rh2(OAc)4 Multicatalysis through Michael Addition/Cyclization Sequence.” Journal of Organic Chemistry, vol. 83, no. 19, Sep. 2018, pp. 12171-12183. https://doi.org/10.1021/acs.joc.8b02127.