Home / Publications / First example of isatin used in four-component synthesis of ionic unsymmetrical scaffold with three different heterocyclic rings

First example of isatin used in four-component synthesis of ionic unsymmetrical scaffold with three different heterocyclic rings

, 
Yuliya Evgenievna Ryzhkova 1
Yuliya Evgenievna Ryzhkova
, 
Varvara Mikhailovna Kalashnikova 1
Varvara Mikhailovna Kalashnikova
, 
Alexander Olegovich Chizhov 1
Alexander Olegovich Chizhov
, 
Artem Nikolaevich Fakhrutdinov 1
Artem Nikolaevich Fakhrutdinov
, 
Mikhail Petrovich Egorov 1
Mikhail Petrovich Egorov
10.1016/j.mencom.2024.10.030
Published 2024-10-22
Communication , Volume 34, Issue 6, 865-867
0
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Elinson M. N. et al. First example of isatin used in four-component synthesis of ionic unsymmetrical scaffold with three different heterocyclic rings // Mendeleev Communications. 2024. Vol. 34. No. 6. pp. 865-867.
GOST all authors (up to 50) Copy
Elinson M. N., Ryzhkova Y. E., Kalashnikova V. M., Chizhov A. O., Fakhrutdinov A. N., Egorov M. P. First example of isatin used in four-component synthesis of ionic unsymmetrical scaffold with three different heterocyclic rings // Mendeleev Communications. 2024. Vol. 34. No. 6. pp. 865-867.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2024.10.030
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.10.030
TI - First example of isatin used in four-component synthesis of ionic unsymmetrical scaffold with three different heterocyclic rings
T2 - Mendeleev Communications
AU - Elinson, Michail Nikolaevich
AU - Ryzhkova, Yuliya Evgenievna
AU - Kalashnikova, Varvara Mikhailovna
AU - Chizhov, Alexander Olegovich
AU - Fakhrutdinov, Artem Nikolaevich
AU - Egorov, Mikhail Petrovich
PY - 2024
DA - 2024/10/22
PB - Mendeleev Communications
SP - 865-867
IS - 6
VL - 34
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2024_Elinson,
author = {Michail Nikolaevich Elinson and Yuliya Evgenievna Ryzhkova and Varvara Mikhailovna Kalashnikova and Alexander Olegovich Chizhov and Artem Nikolaevich Fakhrutdinov and Mikhail Petrovich Egorov},
title = {First example of isatin used in four-component synthesis of ionic unsymmetrical scaffold with three different heterocyclic rings},
journal = {Mendeleev Communications},
year = {2024},
volume = {34},
publisher = {Mendeleev Communications},
month = {Oct},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.10.030},
number = {6},
pages = {865--867},
doi = {10.1016/j.mencom.2024.10.030}
}
MLA
Cite this
MLA Copy
Elinson, Michail Nikolaevich, et al. “First example of isatin used in four-component synthesis of ionic unsymmetrical scaffold with three different heterocyclic rings.” Mendeleev Communications, vol. 34, no. 6, Oct. 2024, pp. 865-867. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.10.030.

Keywords

barbituric acid
four-component reaction
ionic scaffold.
isatin
malononitrile
morpholine
multicomponent reaction
tandem Knoevenagel–Michael reaction

Abstract

The new type of four-component tandem Knoevenagel-Michael reaction was found: isatins, barbituric acids, malononitrile and morpholine at ambient temperature and without catalysts selectively form new non-symmetrical ionic scaffold, namely, morpholin-4-ium 5-(3-dicyanomethyl-2-oxoindolin-3-yl)-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetra-hydropyrimidin-4-olate derivatives, in 80-98% yields. Their structure was confirmed using 2D NMR such as 1H-1H COSY, 1H-13C HSQC, and 1H-13C HMBC correlation experiments. The products seem promising as they contain three different pharmacologically active heterocyclic rings.

References

.
The green chemistry paradigm in modern organic synthesis
Zlotin Sergei G., Egorova Ksenia S., Ananikov Valentine P., Akulov Alexey A., Varaksin Mikhail V., Chupakhin Oleg N., Charushin Valery N., Bryliakov Konstantin P., Averin Alexey D., Beletskaya Irina P., Dolengovski Egor L., Budnikova Yulia H., Sinyashin Oleg G., Gafurov Zufar N., Kantyukov Artyom O., et. al.
Russian Chemical Reviews, 2024
.
Pyrimidine-2,4,6-Triones: A New Effective and Selective Class of Matrix Metalloproteinase Inhibitors
Grams F., Brandstetter H., DAlò S., Geppert D., Krell H., Leinert H., Livi V., Menta E., Oliva A., Zimmermann G.
Biological Chemistry, 2001
.
Multicomponent assembling of salicylaldehydes, malononitrile, and 4-hydroxy-6-methyl-2H-pyran-2-one: A fast and efficient approach to medicinally relevant 2-amino-4H-chromene scaffold
Vereshchagin A.N., Elinson M.N., Ryzhkov F.V., Nasybullin R.F., Bobrovsky S.I., Goloveshkin A.S., Egorov M.P.
Comptes Rendus Chimie, 2015
.
Examining barbiturate scaffold for the synthesis of new agents with biological interest
Katsamakas S., Papadopoulos A.G., Kouskoura M.G., Markopoulou C.K., Hadjipavlou-Litina D.
Future Medicinal Chemistry, 2019
.
Natural Product-like Combinatorial Libraries Based on Privileged Structures. 1. General Principles and Solid-Phase Synthesis of Benzopyrans
Nicolaou K.C., Pfefferkorn J.A., Roecker A.J., Cao G.-., Barluenga S., Mitchell H.J.
Journal of the American Chemical Society, 2000
.
4‐Methyl morpholinium bis‐(thio)barbiturates: Synthesis, structure, anticancer evaluation, and CoMFA study
Noroozi Pesyan N., Rashidnejad H., Esmaeili M.A., Safari E., Tunç T., Alilou M., Safavi‐Sohi R., Şahin E.
Journal of the Chinese Chemical Society, 2020
.
Towards resource efficient chemistry: tandem reactions with renewables
Behr A., Vorholt A.J., Ostrowski K.A., Seidensticker T.
Green Chemistry, 2014
.
Metal-free tandem reaction synthesis of spiro-cyclopropyl fused pyrazolin-5-one derivatives
Liu M., Liu C., Zhang J., Xu Y., Dong L.
Organic Chemistry Frontiers, 2019
.
Isatin derivatives as broad-spectrum antiviral agents: the current landscape
Elsaman T., Mohamed M.S., Eltayib E.M., Abdel-aziz H.A., Abdalla A.E., Munir M.U., Mohamed M.A.
Medicinal Chemistry Research, 2022
.
Influence of phendimetrazine maintenance on the reinforcing, subjective, performance, and physiological effects of intranasal cocaine
Stoops W.W., Strickland J.C., Alcorn J.L., Hays L.R., Rayapati A.O., Lile J.A., Rush C.R.
Psychopharmacology, 2019
.
Zwitterionic pyrimidinium adducts as antioxidants with therapeutic potential as nitric oxide scavenger
Barakat A., Al-Majid A.M., Al-Najjar H.J., Mabkhot Y.N., Javaid S., Yousuf S., Choudhary M.I.
European Journal of Medicinal Chemistry, 2014
.
Elinson M.N., Medvedev M.G., Ilovaisky A.I., Merkulova V.M., Zaimovskaya T.A., Nikishin G.I.
Mendeleev Communications, 2013
.
Structure–activity relationships of the oxindole growth hormone secretagogues
Tokunaga T., Hume W.E., Nagamine J., Kawamura T., Taiji M., Nagata R.
Bioorganic and Medicinal Chemistry Letters, 2005
.
Isatin: A Scaffold with Immense Biodiversity
Nath P., Mukherjee A., Mukherjee S., Banerjee S., Das S., Banerjee S.
Mini-Reviews in Medicinal Chemistry, 2020
.
Shaikh S.N., Saqib M., Ahmed M.H., Patel M.S.
Journal of Drug Delivery and Therapeutics, 2019