Home / Publications / One-pot synthesis of cyclopentane-fused 5'-aryl-4-cycloalkylamino-2,2'-bipyridines via the aza-Diels–Alder/SNipso reactions

One-pot synthesis of cyclopentane-fused 5'-aryl-4-cycloalkylamino-2,2'-bipyridines via the aza-Diels–Alder/SNipso reactions

Alexey P Krinochkin 1, 2
Alexey P Krinochkin
, 
Ekaterina S Starnovskaya 1, 2
Ekaterina S Starnovskaya
, 
Maria Igorevna Valieva 1, 2
Maria Igorevna Valieva
, 
Dmitrii Sergeevich Kopchuk 1, 2
Dmitrii Sergeevich Kopchuk
, 
Sougata Santra 2
Sougata Santra
, 
Pavel Alexandrovich Slepukhin 1, 2
Pavel Alexandrovich Slepukhin
, 
Grigory Vasil'evich Zyryanov 1, 2
Grigory Vasil'evich Zyryanov
, 
Adinath Majee 3
Adinath Majee
, 
Oleg Nikolaevich Chupakhin 1, 2
Oleg Nikolaevich Chupakhin
10.1016/j.mencom.2022.07.007
Published 2022-07-01
Communication , Volume 32, Issue 4, 449-451
4
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Krinochkin A. P. et al. One-pot synthesis of cyclopentane-fused 5'-aryl-4-cycloalkylamino-2,2'-bipyridines via the aza-Diels–Alder/SNipso reactions // Mendeleev Communications. 2022. Vol. 32. No. 4. pp. 449-451.
GOST all authors (up to 50) Copy
Krinochkin A. P., Starnovskaya E. S., Valieva M. I., Kopchuk D. S., Santra S., Slepukhin P. A., Zyryanov G. V., Majee A., Chupakhin O. N. One-pot synthesis of cyclopentane-fused 5'-aryl-4-cycloalkylamino-2,2'-bipyridines via the aza-Diels–Alder/SNipso reactions // Mendeleev Communications. 2022. Vol. 32. No. 4. pp. 449-451.
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TY - JOUR
DO - 10.1016/j.mencom.2022.07.007
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.07.007
TI - One-pot synthesis of cyclopentane-fused 5'-aryl-4-cycloalkylamino-2,2'-bipyridines via the aza-Diels–Alder/SNipso reactions
T2 - Mendeleev Communications
AU - Krinochkin, Alexey P
AU - Starnovskaya, Ekaterina S
AU - Valieva, Maria Igorevna
AU - Kopchuk, Dmitrii Sergeevich
AU - Santra, Sougata
AU - Slepukhin, Pavel Alexandrovich
AU - Zyryanov, Grigory Vasil'evich
AU - Majee, Adinath
AU - Chupakhin, Oleg Nikolaevich
PY - 2022
DA - 2022/07/01
PB - Mendeleev Communications
SP - 449-451
IS - 4
VL - 32
ER -
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@article{2022_Krinochkin,
author = {Alexey P Krinochkin and Ekaterina S Starnovskaya and Maria Igorevna Valieva and Dmitrii Sergeevich Kopchuk and Sougata Santra and Pavel Alexandrovich Slepukhin and Grigory Vasil'evich Zyryanov and Adinath Majee and Oleg Nikolaevich Chupakhin},
title = {One-pot synthesis of cyclopentane-fused 5'-aryl-4-cycloalkylamino-2,2'-bipyridines via the aza-Diels–Alder/SNipso reactions},
journal = {Mendeleev Communications},
year = {2022},
volume = {32},
publisher = {Mendeleev Communications},
month = {Jul},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.07.007},
number = {4},
pages = {449--451},
doi = {10.1016/j.mencom.2022.07.007}
}
MLA
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Krinochkin, Alexey P., et al. “One-pot synthesis of cyclopentane-fused 5'-aryl-4-cycloalkylamino-2,2'-bipyridines via the aza-Diels–Alder/SNipso reactions.” Mendeleev Communications, vol. 32, no. 4, Jul. 2022, pp. 449-451. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.07.007.

Keywords

aza-Diels–Alder reaction
ipso-substitution
124-triazines
2'-bipyridines
amino-2
enamines
one-pot synthesis
solvent-free reaction

Abstract

One-pot synthesis of cyclopentane-fused 5'-aryl-4- cycloalkylamino-2,2'-bipyridines based on the neat (200 °C) reaction of 3-(4-bromopyridin-2-yl)-1,2,4-triazines with enamines is reported. In the course of the transformation, consecutive aza-Diels–Alder reaction and nucleophilic substitution of bromine atom under the action of the liberating amine occur. The possibility of the solvent- and catalyst-free replacement of 4-positioned bromine atom in 2,2'-bipyridines by amino moieties was demonstrated.

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