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Diastereoselective synthesis of 3-substituted acylamino-3,4-dihydro-1,2,4-triazinones

Ilya Nikolayevich Egorov 1
Ilya Nikolayevich Egorov
, 
Burkhard König 2
Burkhard König
, 
Vladimir Leonidovich Rusinov 1
Vladimir Leonidovich Rusinov
, 
Oleg Nikolaevich Chupakhin 1, 3
Oleg Nikolaevich Chupakhin
10.1016/j.mencom.2008.03.017
Published 2008-03-18
Communication , Volume 18, Issue 2, 99-101
7
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Egorov I. N. et al. Diastereoselective synthesis of 3-substituted acylamino-3,4-dihydro-1,2,4-triazinones // Mendeleev Communications. 2008. Vol. 18. No. 2. pp. 99-101.
GOST all authors (up to 50) Copy
Egorov I. N., König B., Rusinov V. L., Chupakhin O. N. Diastereoselective synthesis of 3-substituted acylamino-3,4-dihydro-1,2,4-triazinones // Mendeleev Communications. 2008. Vol. 18. No. 2. pp. 99-101.
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TY - JOUR
DO - 10.1016/j.mencom.2008.03.017
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2008.03.017
TI - Diastereoselective synthesis of 3-substituted acylamino-3,4-dihydro-1,2,4-triazinones
T2 - Mendeleev Communications
AU - Egorov, Ilya Nikolayevich
AU - König, Burkhard
AU - Rusinov, Vladimir Leonidovich
AU - Chupakhin, Oleg Nikolaevich
PY - 2008
DA - 2008/03/18
PB - Mendeleev Communications
SP - 99-101
IS - 2
VL - 18
ER -
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@article{2008_Egorov,
author = {Ilya Nikolayevich Egorov and Burkhard König and Vladimir Leonidovich Rusinov and Oleg Nikolaevich Chupakhin},
title = {Diastereoselective synthesis of 3-substituted acylamino-3,4-dihydro-1,2,4-triazinones},
journal = {Mendeleev Communications},
year = {2008},
volume = {18},
publisher = {Mendeleev Communications},
month = {Mar},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2008.03.017},
number = {2},
pages = {99--101},
doi = {10.1016/j.mencom.2008.03.017}
}
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Egorov, Ilya Nikolayevich, et al. “Diastereoselective synthesis of 3-substituted acylamino-3,4-dihydro-1,2,4-triazinones.” Mendeleev Communications, vol. 18, no. 2, Mar. 2008, pp. 99-101. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2008.03.017.

Keywords

1.2.4-triazines
amino acids
diastereoselective synthesis
indoles

Abstract

6-Phenyl-1,2,4-triazin-5(4H)-one 1 reacts with C-nucleophiles, such as indole, in the presence of N-acetylamino acids, to yield 2-acyl-3-indolyl-6-phenyl-3,4-dihydro-1,2,4-triazin-5(4H)-ones 2–6 with high diastereoselectivity.

References

1.
Asymmetric induction in the nucleophilic addition in the series of aromatic azines
Egorov I.N., Zyryanov G.V., Rusinov V.L., Chupakhin O.N.
Russian Chemical Reviews, 2005
4.
10.1016/j.mencom.2008.03.017_bib4
Sieck
Synlett, 2003
5.
Asymmetric Synthesis of Isoquinoline Derivatives from Amino Acids
Sieck O., Ehwald M., Liebscher J.
European Journal of Organic Chemistry, 2005
6.
Asymmetric induction in the reactions of 3-aryl-1,2,4-triazin-5(4H)-ones with C-nucleophiles
Egorov I.N., Zyryanov G.V., Ulomsky E.N., Rusinov V.L., Chupakhin O.N.
Tetrahedron Letters, 2006