Transition-Metal-Free, Atom- and Step-Economic Synthesis of Aminoketopyrrolizines from Benzylamine, Acylethynylpyrroles, and Acylacetylenes
Publication type: Journal Article
Publication date: 2017-03-21
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
28322568
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
A concise, atom-economic strategy for the synthesis of pyrrolizines with amino and keto substituents has been developed. It includes the following key steps: (i) the base-catalyzed (K3PO4/DMSO) addition of a benzylamine to 2-acylethynylpyrroles and (ii) noncatalyzed addition of enaminones obtained to the triple bond of acylacetylenes followed by intramolecular cyclization of the intermediate pentadiendiones thus formed to the target 1-(benzylamino)-2-acyl-3-methylenoacylpyrrolizines.
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Total citations:
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Citations from 2024:
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(7.69%)
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Sobenina L. N. et al. Transition-Metal-Free, Atom- and Step-Economic Synthesis of Aminoketopyrrolizines from Benzylamine, Acylethynylpyrroles, and Acylacetylenes // Organic Letters. 2017. Vol. 19. No. 7. pp. 1586-1589.
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Sobenina L. N., Tomilin D. N., Sagitova E. F., Ushakov I., Trofimov B. A. Transition-Metal-Free, Atom- and Step-Economic Synthesis of Aminoketopyrrolizines from Benzylamine, Acylethynylpyrroles, and Acylacetylenes // Organic Letters. 2017. Vol. 19. No. 7. pp. 1586-1589.
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TY - JOUR
DO - 10.1021/acs.orglett.7b00408
UR - https://doi.org/10.1021/acs.orglett.7b00408
TI - Transition-Metal-Free, Atom- and Step-Economic Synthesis of Aminoketopyrrolizines from Benzylamine, Acylethynylpyrroles, and Acylacetylenes
T2 - Organic Letters
AU - Sobenina, Lyubov N.
AU - Tomilin, Denis N.
AU - Sagitova, Elena F.
AU - Ushakov, Igor
AU - Trofimov, B. A.
PY - 2017
DA - 2017/03/21
PB - American Chemical Society (ACS)
SP - 1586-1589
IS - 7
VL - 19
PMID - 28322568
SN - 1523-7060
SN - 1523-7052
ER -
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BibTex (up to 50 authors)
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@article{2017_Sobenina,
author = {Lyubov N. Sobenina and Denis N. Tomilin and Elena F. Sagitova and Igor Ushakov and B. A. Trofimov},
title = {Transition-Metal-Free, Atom- and Step-Economic Synthesis of Aminoketopyrrolizines from Benzylamine, Acylethynylpyrroles, and Acylacetylenes},
journal = {Organic Letters},
year = {2017},
volume = {19},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://doi.org/10.1021/acs.orglett.7b00408},
number = {7},
pages = {1586--1589},
doi = {10.1021/acs.orglett.7b00408}
}
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MLA
Copy
Sobenina, Lyubov N., et al. “Transition-Metal-Free, Atom- and Step-Economic Synthesis of Aminoketopyrrolizines from Benzylamine, Acylethynylpyrroles, and Acylacetylenes.” Organic Letters, vol. 19, no. 7, Mar. 2017, pp. 1586-1589. https://doi.org/10.1021/acs.orglett.7b00408.