Base-promoted cyclization of 3-alkynylquinoxaline-2-carbonitriles with CH-acids: a new method for the phenazine ring synthesis
Publication type: Journal Article
Publication date: 2014-08-01
scimago Q3
wos Q2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
3-Alkynylquinoxaline-2-carbonitriles were directly transformed into 2,3-disubstituted phenazin-1-amines by treating with a CH-acid (diethylmalonate, ethyl cyanoacetate, malononitrile, 2-tosylacetonitrile, 2-(1-methyl-1H-benzo[d]imidazol-2-yl)acetonitrile, nitromethane) and t-BuOK in THF or DMSO. A new cascade process includes nucleophilic addition of a CH-acid carbanion to the C C bond of 3-alkynylquinoxaline-2-carbonitrile, 6-exo-dig cyclization of the intermediate allyl carbanion with the formation of 2,2-disubstituted 1-imino-1,2-dihydrophenazine and its aromatization via elimination of the C(2)-substituent. Several secondary reactions were also disclosed and discussed.
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Total citations:
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Citations from 2024:
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Nguyen H. T. L. et al. Base-promoted cyclization of 3-alkynylquinoxaline-2-carbonitriles with CH-acids: a new method for the phenazine ring synthesis // Tetrahedron. 2014. Vol. 70. No. 31. pp. 4617-4625.
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Nguyen H. T. L., Gulevskaya A. V., Pozharskii A. F., Nelina Nemtseva J. I. Base-promoted cyclization of 3-alkynylquinoxaline-2-carbonitriles with CH-acids: a new method for the phenazine ring synthesis // Tetrahedron. 2014. Vol. 70. No. 31. pp. 4617-4625.
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TY - JOUR
DO - 10.1016/j.tet.2014.05.023
UR - https://doi.org/10.1016/j.tet.2014.05.023
TI - Base-promoted cyclization of 3-alkynylquinoxaline-2-carbonitriles with CH-acids: a new method for the phenazine ring synthesis
T2 - Tetrahedron
AU - Nguyen, Huong T L
AU - Gulevskaya, Anna V
AU - Pozharskii, Alexander F.
AU - Nelina Nemtseva, Julia I
PY - 2014
DA - 2014/08/01
PB - Elsevier
SP - 4617-4625
IS - 31
VL - 70
SN - 0040-4020
SN - 1464-5416
ER -
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BibTex (up to 50 authors)
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@article{2014_Nguyen,
author = {Huong T L Nguyen and Anna V Gulevskaya and Alexander F. Pozharskii and Julia I Nelina Nemtseva},
title = {Base-promoted cyclization of 3-alkynylquinoxaline-2-carbonitriles with CH-acids: a new method for the phenazine ring synthesis},
journal = {Tetrahedron},
year = {2014},
volume = {70},
publisher = {Elsevier},
month = {aug},
url = {https://doi.org/10.1016/j.tet.2014.05.023},
number = {31},
pages = {4617--4625},
doi = {10.1016/j.tet.2014.05.023}
}
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MLA
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Nguyen, Huong T. L., et al. “Base-promoted cyclization of 3-alkynylquinoxaline-2-carbonitriles with CH-acids: a new method for the phenazine ring synthesis.” Tetrahedron, vol. 70, no. 31, Aug. 2014, pp. 4617-4625. https://doi.org/10.1016/j.tet.2014.05.023.