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β-Carbolines as intermediates in indirect heteroarylation of tryptamines exemplified by the synthesis of 2-pyrazolyltryptamines

Alexander Aleksandrovich Zubenko 1
Alexander Aleksandrovich Zubenko
, 
Lyudmila Nikolaevna Divaeva 2
Lyudmila Nikolaevna Divaeva
, 
Anatolii Savel'evich Morkovnik 2
Anatolii Savel'evich Morkovnik
, 
Vadim Sergeevich Sochnev 2
Vadim Sergeevich Sochnev
,  , 
Viktorya Vladimirovna Chekrysheva 1
Viktorya Vladimirovna Chekrysheva
, 
Alexander Ivanovich Klimenko 1
Alexander Ivanovich Klimenko
, 
Alexandra Evgen'evna Svyatogorova 1
Alexandra Evgen'evna Svyatogorova
1 North-Caucasian Zonal Research Veterinary Institute, Novocherkassk, Russian Federation
2 Institute of Physical and Organic Chemistry, Southern Federal University, Rostov-on-Don, Russian Federation
3 North-Caucasus Federal University, Stavropol, Russian Federation
10.1016/j.mencom.2023.09.018
Published 2023-09-01
Communication , Volume 33, Issue 5, 645-647
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Zubenko A. A. et al. β-Carbolines as intermediates in indirect heteroarylation of tryptamines exemplified by the synthesis of 2-pyrazolyltryptamines // Mendeleev Communications. 2023. Vol. 33. No. 5. pp. 645-647.
GOST all authors (up to 50) Copy
Zubenko A. A., Divaeva L. N., Morkovnik A. S., Sochnev V. S., Demidov O. P., Chekrysheva V. V., Klimenko A. I., Svyatogorova A. E. β-Carbolines as intermediates in indirect heteroarylation of tryptamines exemplified by the synthesis of 2-pyrazolyltryptamines // Mendeleev Communications. 2023. Vol. 33. No. 5. pp. 645-647.
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TY - JOUR
DO - 10.1016/j.mencom.2023.09.018
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.09.018
TI - β-Carbolines as intermediates in indirect heteroarylation of tryptamines exemplified by the synthesis of 2-pyrazolyltryptamines
T2 - Mendeleev Communications
AU - Zubenko, Alexander Aleksandrovich
AU - Divaeva, Lyudmila Nikolaevna
AU - Morkovnik, Anatolii Savel'evich
AU - Sochnev, Vadim Sergeevich
AU - Demidov, Oleg Petrovich
AU - Chekrysheva, Viktorya Vladimirovna
AU - Klimenko, Alexander Ivanovich
AU - Svyatogorova, Alexandra Evgen'evna
PY - 2023
DA - 2023/09/01
PB - Mendeleev Communications
SP - 645-647
IS - 5
VL - 33
ER -
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@article{2023_Zubenko,
author = {Alexander Aleksandrovich Zubenko and Lyudmila Nikolaevna Divaeva and Anatolii Savel'evich Morkovnik and Vadim Sergeevich Sochnev and Oleg Petrovich Demidov and Viktorya Vladimirovna Chekrysheva and Alexander Ivanovich Klimenko and Alexandra Evgen'evna Svyatogorova},
title = {β-Carbolines as intermediates in indirect heteroarylation of tryptamines exemplified by the synthesis of 2-pyrazolyltryptamines},
journal = {Mendeleev Communications},
year = {2023},
volume = {33},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.09.018},
number = {5},
pages = {645--647},
doi = {10.1016/j.mencom.2023.09.018}
}
MLA
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Zubenko, Alexander Aleksandrovich, et al. “β-Carbolines as intermediates in indirect heteroarylation of tryptamines exemplified by the synthesis of 2-pyrazolyltryptamines.” Mendeleev Communications, vol. 33, no. 5, Sep. 2023, pp. 645-647. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.09.018.

Keywords

1-aroylmethylidene-1
2
2-(pyrazol-3-yl)-O-methylserotonins
2-(pyrazol-3-yl)tryptamine
3
4-tetrahydro-β-carbolines
pyrazolylmelatonins
quantum chemical calculations.
recyclization
tryptamines
β-carbolines

Abstract

A cyclization-recyclization pathway for indirect 2-heteroarylation of tryptamines has been suggested by the example of introducing the pyrazolyl moiety. The process involves the intermediate cyclization of tryptamines into push-pull type β-carboline semi-products. The relative stability of the tautomeric forms of 2-pyrazolyltryptamines has been estimated using the DFT method.

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