Intramolecular 1,3-dipolar cycloaddition of azomethine ylides generated from ethoxycarbonylcarbenoids and Schiff bases
Publication type: Journal Article
Publication date: 2005-09-01
scimago Q4
wos Q4
SJR: 0.190
CiteScore: 1.3
Impact factor: 0.9
ISSN: 10704280, 16083393
Organic Chemistry
Abstract
Decomposition of ethyl diazoacetate in the presence of copper, copper acetylacetonate, or copper trifluoroacetylacetonate and ethyl 4-[2-(R-imino)phenoxymethyl]-2-butenoate leads to formation of chromeno-[4,3-b]pyrrole-2,3-dicarboxylic acid derivatives. The reactions involve intermediate formation of azomethine ylides which undergo regio- and stereoselective intramolecular cycloaddition at the C=C bond to afford chromeno[4,3-b]pyrroles. The steric structure of the product depends on the configuration of intermediate ylide and nature of the substituent at the ylide nitrogen atom.
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Khlebnikov A. F. et al. Intramolecular 1,3-dipolar cycloaddition of azomethine ylides generated from ethoxycarbonylcarbenoids and Schiff bases // Russian Journal of Organic Chemistry. 2005. Vol. 41. No. 9. pp. 1341-1348.
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Khlebnikov A. F., Novikov M., Kostikov R. R., Kopf J. Intramolecular 1,3-dipolar cycloaddition of azomethine ylides generated from ethoxycarbonylcarbenoids and Schiff bases // Russian Journal of Organic Chemistry. 2005. Vol. 41. No. 9. pp. 1341-1348.
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RIS
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TY - JOUR
DO - 10.1007/s11178-005-0344-2
UR - https://doi.org/10.1007/s11178-005-0344-2
TI - Intramolecular 1,3-dipolar cycloaddition of azomethine ylides generated from ethoxycarbonylcarbenoids and Schiff bases
T2 - Russian Journal of Organic Chemistry
AU - Khlebnikov, A F
AU - Novikov, M.S.
AU - Kostikov, R R
AU - Kopf, J.
PY - 2005
DA - 2005/09/01
PB - Pleiades Publishing
SP - 1341-1348
IS - 9
VL - 41
SN - 1070-4280
SN - 1608-3393
ER -
Cite this
BibTex (up to 50 authors)
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@article{2005_Khlebnikov,
author = {A F Khlebnikov and M.S. Novikov and R R Kostikov and J. Kopf},
title = {Intramolecular 1,3-dipolar cycloaddition of azomethine ylides generated from ethoxycarbonylcarbenoids and Schiff bases},
journal = {Russian Journal of Organic Chemistry},
year = {2005},
volume = {41},
publisher = {Pleiades Publishing},
month = {sep},
url = {https://doi.org/10.1007/s11178-005-0344-2},
number = {9},
pages = {1341--1348},
doi = {10.1007/s11178-005-0344-2}
}
Cite this
MLA
Copy
Khlebnikov, A. F., et al. “Intramolecular 1,3-dipolar cycloaddition of azomethine ylides generated from ethoxycarbonylcarbenoids and Schiff bases.” Russian Journal of Organic Chemistry, vol. 41, no. 9, Sep. 2005, pp. 1341-1348. https://doi.org/10.1007/s11178-005-0344-2.
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