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Formation of 3-Amino-1,2,4-triazines by Thermolysis of Condensed N-Amino-α-Azidoimidazoles

Alexander Fedorovich Pozharskii 1
Alexander Fedorovich Pozharskii
, 
Ilya M Nanavyan 2
Ilya M Nanavyan
, 
Valery Vasil'evich Kuz'menko 2
Valery Vasil'evich Kuz'menko
10.1070/MC1992v002n01ABEH000114
Published 1992-03-31
Communication , Volume 2, Issue 1, 33-35
4
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Pozharskii A. F., Nanavyan I. M., Kuz'menko V. V. Formation of 3-Amino-1,2,4-triazines by Thermolysis of Condensed N-Amino-α-Azidoimidazoles // Mendeleev Communications. 1992. Vol. 2. No. 1. pp. 33-35.
GOST all authors (up to 50) Copy
Pozharskii A. F., Nanavyan I. M., Kuz'menko V. V. Formation of 3-Amino-1,2,4-triazines by Thermolysis of Condensed N-Amino-α-Azidoimidazoles // Mendeleev Communications. 1992. Vol. 2. No. 1. pp. 33-35.
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TY - JOUR
DO - 10.1070/MC1992v002n01ABEH000114
UR - https://mendcomm.colab.ws/publications/10.1070/MC1992v002n01ABEH000114
TI - Formation of 3-Amino-1,2,4-triazines by Thermolysis of Condensed N-Amino-α-Azidoimidazoles
T2 - Mendeleev Communications
AU - Pozharskii, Alexander Fedorovich
AU - Nanavyan, Ilya M
AU - Kuz'menko, Valery Vasil'evich
PY - 1992
DA - 1992/03/31
PB - Mendeleev Communications
SP - 33-35
IS - 1
VL - 2
ER -
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@article{1992_Pozharskii,
author = {Alexander Fedorovich Pozharskii and Ilya M Nanavyan and Valery Vasil'evich Kuz'menko},
title = {Formation of 3-Amino-1,2,4-triazines by Thermolysis of Condensed N-Amino-α-Azidoimidazoles},
journal = {Mendeleev Communications},
year = {1992},
volume = {2},
publisher = {Mendeleev Communications},
month = {Mar},
url = {https://mendcomm.colab.ws/publications/10.1070/MC1992v002n01ABEH000114},
number = {1},
pages = {33--35},
doi = {10.1070/MC1992v002n01ABEH000114}
}
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Pozharskii, Alexander Fedorovich, et al. “Formation of 3-Amino-1,2,4-triazines by Thermolysis of Condensed N-Amino-α-Azidoimidazoles.” Mendeleev Communications, vol. 2, no. 1, Mar. 1992, pp. 33-35. https://mendcomm.colab.ws/publications/10.1070/MC1992v002n01ABEH000114.

Abstract

1-Amino-2-azidobenzimidazole 7, 7-amino-8-azido- 9 and 9-amino-8-azido-theophillines 12, on heating in chlorobenzene solution, lose a molecule of nitrogen and finally give 3-amino-derivatives of benzo-1,2,4-triazine 3, 5,7-dimethylpyrimido[4,5-e]-1,2,4-triazine-6,8-dione 10 (isofervenulin) and 6,8-dimethylpyrimido[5,4-e]-1,2,4-triazine- 5,7-dione 13 (fervenulin) in good yields; the reaction is thought to proceed through the recyclization of an intermediate C-nitrene of type 4.

References

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Oxidation of 1,2-diaminobenzimidazoles to 3-amino-1,2,4-benzotriazines
Zeiger A.V., Joullie M.M.
Journal of Organic Chemistry, 1977
2.
Manganese dioxide oxidation of aryl 1,2-diaminoimidazoles
Nakajima M., Hisada R., Anselme J.P.
Journal of Organic Chemistry, 1978
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