Home / Publications / Synthesis of 2-amino-3,6-di(het)arylpyridines from 5-cyano-3,6-di(het)aryl-1,2,4-triazines and arylhydrazines via the \( \mathrm{S_N^{ipso}} \)/aza-Diels-Alder reaction sequence

Synthesis of 2-amino-3,6-di(het)arylpyridines from 5-cyano-3,6-di(het)aryl-1,2,4-triazines and arylhydrazines via the \( \mathrm{S_N^{ipso}} \)/aza-Diels-Alder reaction sequence

Alexey P Krinochkin 1, 2
Alexey P Krinochkin
, 
Mallikarjuna Reddy Guda 2
Mallikarjuna Reddy Guda
, 
Alluru Rammohan 2
Alluru Rammohan
, 
Dmitrii Sergeevich Kopchuk 1, 2
Dmitrii Sergeevich Kopchuk
, 
Igor Leonidovich Nikonov 1, 2
Igor Leonidovich Nikonov
, 
Evgeny Dmitrievich Ladin 2
Evgeny Dmitrievich Ladin
, 
Sougata Santra 2
Sougata Santra
, 
Ilya Nikolayevich Egorov 2
Ilya Nikolayevich Egorov
, 
Grigory Vasil'evich Zyryanov 1, 2
Grigory Vasil'evich Zyryanov
, 
Oleg Nikolaevich Chupakhin 2
Oleg Nikolaevich Chupakhin
10.1016/j.mencom.2022.11.006
Published 2022-10-21
Communication , Volume 32, Issue 6, 726-728
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Krinochkin A. P. et al. Synthesis of 2-amino-3,6-di(het)arylpyridines from 5-cyano-3,6-di(het)aryl-1,2,4-triazines and arylhydrazines via the \( \mathrm{S_N^{ipso}} \)/aza-Diels-Alder reaction sequence // Mendeleev Communications. 2022. Vol. 32. No. 6. pp. 726-728.
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Krinochkin A. P., Guda M. R., Rammohan A., Kopchuk D. S., Nikonov I. L., Ladin E. D., Santra S., Egorov I. N., Zyryanov G. V., Chupakhin O. N. Synthesis of 2-amino-3,6-di(het)arylpyridines from 5-cyano-3,6-di(het)aryl-1,2,4-triazines and arylhydrazines via the \( \mathrm{S_N^{ipso}} \)/aza-Diels-Alder reaction sequence // Mendeleev Communications. 2022. Vol. 32. No. 6. pp. 726-728.
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TY - JOUR
DO - 10.1016/j.mencom.2022.11.006
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.11.006
TI - Synthesis of 2-amino-3,6-di(het)arylpyridines from 5-cyano-3,6-di(het)aryl-1,2,4-triazines and arylhydrazines via the \( \mathrm{S_N^{ipso}} \)/aza-Diels-Alder reaction sequence
T2 - Mendeleev Communications
AU - Krinochkin, Alexey P
AU - Guda, Mallikarjuna Reddy
AU - Rammohan, Alluru
AU - Kopchuk, Dmitrii Sergeevich
AU - Nikonov, Igor Leonidovich
AU - Ladin, Evgeny Dmitrievich
AU - Santra, Sougata
AU - Egorov, Ilya Nikolayevich
AU - Zyryanov, Grigory Vasil'evich
AU - Chupakhin, Oleg Nikolaevich
PY - 2022
DA - 2022/10/21
PB - Mendeleev Communications
SP - 726-728
IS - 6
VL - 32
ER -
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@article{2022_Krinochkin,
author = {Alexey P Krinochkin and Mallikarjuna Reddy Guda and Alluru Rammohan and Dmitrii Sergeevich Kopchuk and Igor Leonidovich Nikonov and Evgeny Dmitrievich Ladin and Sougata Santra and Ilya Nikolayevich Egorov and Grigory Vasil'evich Zyryanov and Oleg Nikolaevich Chupakhin},
title = {Synthesis of 2-amino-3,6-di(het)arylpyridines from 5-cyano-3,6-di(het)aryl-1,2,4-triazines and arylhydrazines via the \( \mathrm{S_N^{ipso}} \)/aza-Diels-Alder reaction sequence},
journal = {Mendeleev Communications},
year = {2022},
volume = {32},
publisher = {Mendeleev Communications},
month = {Oct},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.11.006},
number = {6},
pages = {726--728},
doi = {10.1016/j.mencom.2022.11.006}
}
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Krinochkin, Alexey P., et al. “Synthesis of 2-amino-3,6-di(het)arylpyridines from 5-cyano-3,6-di(het)aryl-1,2,4-triazines and arylhydrazines via the \( \mathrm{S_N^{ipso}} \)/aza-Diels-Alder reaction sequence.” Mendeleev Communications, vol. 32, no. 6, Oct. 2022, pp. 726-728. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.11.006.
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Keywords

1,2,4-triazines
2-aminopyridines
6-amino-2,2'-bipyridines
arylhydrazines
autoclave processes
aza-Diels-Alder reaction
ipso-substitution

Abstract

Reaction between 5-cyano-3,6-di(het)aryl-1,2,4-triazines and arylhydrazines with the following aza-Diels-Alder autoclave reaction affords hardly available 2-amino-3,6-di(het)aryl-pyridines in up to 67% yield after two steps and in 75% yield for the one-pot way. The compounds obtained can be promising for medicinal chemistry.

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