Synthesis and Intramolecular Azo Coupling of 4-Diazopyrrole-2-carboxylates: Selective Approach to Benzo and Hetero [c]-Fused 6H-Pyrrolo[3,4-c]pyridazine-5-carboxylates
Тип публикации: Journal Article
Дата публикации: 2016-08-31
scimago Q2
wos Q1
БС1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
27548333
Organic Chemistry
Краткое описание
A high yield synthesis of fluorescent benzo, thieno, and furo [c]-fused methyl 7-aryl-6H-pyrrolo[3,4-c]pyridazine-5-carboxylates, including unprecedented heterocyclic skeletons, was performed by the transformation of methyl 4-aminopyrrole-2-carboxylate into the corresponding diazo compound, followed by intramolecular azo coupling under acid conditions onto a nucleophilic aryl or hetaryl group in the 3-position. Azo coupling is completely regioselective and, according to DFT calculations, a kinetically controlled reaction. N-Methylation of 1,3-disubstituted 2H-pyrrolo[3,4-c]cinnolines occurs selectively at N5 under kinetic control, leading exclusively to 5-methyl-5H-pyrrolo[3,4-c]cinnoline derivatives.
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Galenko E. E. et al. Synthesis and Intramolecular Azo Coupling of 4-Diazopyrrole-2-carboxylates: Selective Approach to Benzo and Hetero [c]-Fused 6H-Pyrrolo[3,4-c]pyridazine-5-carboxylates // Journal of Organic Chemistry. 2016. Vol. 81. No. 18. pp. 8495-8507.
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Galenko E. E., Galenko A. V., Khlebnikov A. F., Novikov M. S., Shakirova J. R. Synthesis and Intramolecular Azo Coupling of 4-Diazopyrrole-2-carboxylates: Selective Approach to Benzo and Hetero [c]-Fused 6H-Pyrrolo[3,4-c]pyridazine-5-carboxylates // Journal of Organic Chemistry. 2016. Vol. 81. No. 18. pp. 8495-8507.
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TY - JOUR
DO - 10.1021/acs.joc.6b01662
UR - https://doi.org/10.1021/acs.joc.6b01662
TI - Synthesis and Intramolecular Azo Coupling of 4-Diazopyrrole-2-carboxylates: Selective Approach to Benzo and Hetero [c]-Fused 6H-Pyrrolo[3,4-c]pyridazine-5-carboxylates
T2 - Journal of Organic Chemistry
AU - Galenko, Ekaterina E
AU - Galenko, Alexey V
AU - Khlebnikov, Alexander F
AU - Novikov, Mikhail S.
AU - Shakirova, Julia R
PY - 2016
DA - 2016/08/31
PB - American Chemical Society (ACS)
SP - 8495-8507
IS - 18
VL - 81
PMID - 27548333
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2016_Galenko,
author = {Ekaterina E Galenko and Alexey V Galenko and Alexander F Khlebnikov and Mikhail S. Novikov and Julia R Shakirova},
title = {Synthesis and Intramolecular Azo Coupling of 4-Diazopyrrole-2-carboxylates: Selective Approach to Benzo and Hetero [c]-Fused 6H-Pyrrolo[3,4-c]pyridazine-5-carboxylates},
journal = {Journal of Organic Chemistry},
year = {2016},
volume = {81},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://doi.org/10.1021/acs.joc.6b01662},
number = {18},
pages = {8495--8507},
doi = {10.1021/acs.joc.6b01662}
}
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Galenko, Ekaterina E., et al. “Synthesis and Intramolecular Azo Coupling of 4-Diazopyrrole-2-carboxylates: Selective Approach to Benzo and Hetero [c]-Fused 6H-Pyrrolo[3,4-c]pyridazine-5-carboxylates.” Journal of Organic Chemistry, vol. 81, no. 18, Aug. 2016, pp. 8495-8507. https://doi.org/10.1021/acs.joc.6b01662.