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Catalyst-free three-component synthesis of hydroxyalkyltriazolylmethylidene barbiturates

Maria Matveevna Demina 1
Maria Matveevna Demina
, 
Alevtina Sergeevna Medvedeva 1
Alevtina Sergeevna Medvedeva
, 
Tran D Vu 2
Tran D Vu
, 
Lyudmila Ivanovna Larina 1
Lyudmila Ivanovna Larina
, 
Inessa Vasil'evna Mitroshina 1
Inessa Vasil'evna Mitroshina
, 
Olesya Aleksandrovna Shemyakina 1
Olesya Aleksandrovna Shemyakina
10.1016/j.mencom.2019.11.017
Published 2019-11-01
Communication , Volume 29, Issue 6, 655-657
4
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Demina M. M. et al. Catalyst-free three-component synthesis of hydroxyalkyltriazolylmethylidene barbiturates // Mendeleev Communications. 2019. Vol. 29. No. 6. pp. 655-657.
GOST all authors (up to 50) Copy
Demina M. M., Medvedeva A. S., Vu T. D., Larina L. I., Mitroshina I. V., Shemyakina O. A. Catalyst-free three-component synthesis of hydroxyalkyltriazolylmethylidene barbiturates // Mendeleev Communications. 2019. Vol. 29. No. 6. pp. 655-657.
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TY - JOUR
DO - 10.1016/j.mencom.2019.11.017
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.11.017
TI - Catalyst-free three-component synthesis of hydroxyalkyltriazolylmethylidene barbiturates
T2 - Mendeleev Communications
AU - Demina, Maria Matveevna
AU - Medvedeva, Alevtina Sergeevna
AU - Vu, Tran D
AU - Larina, Lyudmila Ivanovna
AU - Mitroshina, Inessa Vasil'evna
AU - Shemyakina, Olesya Aleksandrovna
PY - 2019
DA - 2019/11/01
PB - Mendeleev Communications
SP - 655-657
IS - 6
VL - 29
ER -
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@article{2019_Demina,
author = {Maria Matveevna Demina and Alevtina Sergeevna Medvedeva and Tran D Vu and Lyudmila Ivanovna Larina and Inessa Vasil'evna Mitroshina and Olesya Aleksandrovna Shemyakina},
title = {Catalyst-free three-component synthesis of hydroxyalkyltriazolylmethylidene barbiturates},
journal = {Mendeleev Communications},
year = {2019},
volume = {29},
publisher = {Mendeleev Communications},
month = {Nov},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.11.017},
number = {6},
pages = {655--657},
doi = {10.1016/j.mencom.2019.11.017}
}
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Demina, Maria Matveevna, et al. “Catalyst-free three-component synthesis of hydroxyalkyltriazolylmethylidene barbiturates.” Mendeleev Communications, vol. 29, no. 6, Nov. 2019, pp. 655-657. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.11.017.

Abstract

5-[(5-Hydroxyalkyl-1H-1,2,3-triazol-4-yl)methylidene]barbiturates were eco-friendly synthesized in up to 89% yields by one-pot three-component processing (no catalyst, H2O–EtOH, room temperature, 38h) of 4-hydroxyalkynals, trimethylsilylazide and barbituric acids.

References

1.
Multicomponent reactions are accelerated in water.
Pirrung M.C., Sarma K.D.
Journal of the American Chemical Society, 2003
5.
Screening Multicomponent Reactions for X-Linked Inhibitor of Apoptosis-Baculoviral Inhibitor of Apoptosis Protein Repeats Domain Binder
Monfardini I., Huang J., Beck B., Cellitti J.F., Pellecchia M., Dömling A.
Journal of Medicinal Chemistry, 2011
6.
Chemistry and Biology Of Multicomponent Reactions
Dömling A., Wang W., Wang K.
Chemical Reviews, 2012
9.
Multicomponent reactions: a sustainable tool to 1,2- and 1,3-azoles
Preeti P., Singh K.N.
Organic and Biomolecular Chemistry, 2018
11.
Multicomponent Reactions for the Synthesis of Heterocycles
Jiang B., Rajale T., Wever W., Tu S., Li G.
Chemistry - An Asian Journal, 2010
13.
Recent applications of barbituric acid in multicomponent reactions
Mohammadi Ziarani G., Aleali F., Lashgari N.
RSC Advances, 2016
14.
Molecular Hybridization: A Useful Tool in the Design of New Drug Prototypes
Claudio Viegas-Junior, Eliezer J. Barreiro, Carlos Alberto Manssour Fraga
Current Medicinal Chemistry, 2007
16.
Rational approaches, design strategies, structure activity relationship and mechanistic insights for anticancer hybrids.
Nepali K., Sharma S., Sharma M., Bedi P.M., Dhar K.L.
European Journal of Medicinal Chemistry, 2014
17.
10.1016/j.mencom.2019.11.017_sbref0020a
Garcia
Pharmacology and Physiology for Anesthesia: Foundations and Clinical Application, 2019
19.
10.1016/j.mencom.2019.11.017_sbref0020c
Lopez-Munoz
Neuropsychiatr. Dis. Treat., 2005
21.
One-pot Synthesis of 5-{[Bis(azolylmethylthio)]methylene}pyrimidine-2,4,6-(1H,3H,5H)-triones
Padmavathi V., Reddy G.D., Venkatesh B.C., Padmaja A.
Archiv der Pharmazie, 2010
23.
Antimicrobial Efficacy of Metal-Barbiturate Conjugates Against Pathogenic Strains of Escherichia coli and Staphylococcus aureus
Mahmood Qureshi A., Qadir M., Rauf A., Idrees M., Mumtaz S., Najam-ul-Haq M., Ismail M., Athar M., Khushal R., Riaz S., Bokhari H.
Letters in Drug Design and Discovery, 2011
24.
Inhibitory effects of 5-benzylidene barbiturate derivatives on mushroom tyrosinase and their antibacterial activities
Yan Q., Cao R., Yi W., Chen Z., Wen H., Ma L., Song H.
European Journal of Medicinal Chemistry, 2009
25.
10.1016/j.mencom.2019.11.017_sbref0030a
Demopoulos
Acta Neurol. Scand., 1977
26.
Synthesis of 5-Arylidene Barbiturates: A Novel Class of DPPH Radical Scavengers
Khan K.M., Ali M., Ajaz A., Perveen S., Choudhary M.I., Atta-ur-Rahman
Letters in Drug Design and Discovery, 2008
27.
Antibacterial, Antiurease, and Antioxidant Activities of Some Arylidene Barbiturates
Sokmen B.B., Ugras S., Sarikaya H.Y., Ugras H.I., Yanardag R.
Applied Biochemistry and Biotechnology, 2013
29.
10.1016/j.mencom.2019.11.017_sbref0030e
Moon
Oncotarget, 2017
30.
Selective cell adhesion inhibitors: Barbituric acid based α4β7—MAdCAM inhibitors
Harriman G.C., Brewer M., Bennett R., Kuhn C., Bazin M., Larosa G., Skerker P., Cochran N., Gallant D., Baxter D., Picarella D., Jaffee B., Luly J.R., Briskin M.J.
Bioorganic and Medicinal Chemistry Letters, 2008
31.
Synthesis, antioxidant and DNA cleavage activities of novel indole derivatives
Biradar J.S., Sasidhar B.S., Parveen R.
European Journal of Medicinal Chemistry, 2010
32.
Possible Application of the Organic Barbiturates as NLO Materials
Ivanova B.B., Spiteller M.
Crystal Growth and Design, 2010
34.
Spiro copper(II)-metallacycles derived from 5-arylaminomethylene-barbituric acids: Synthesis and structural characterization
Fırıncı E., Giziroglu E., Celepci D.B., Söyleyici H.C., Aygün M.
Journal of Molecular Structure, 2017
35.
Barbituric acids as a useful tool for the construction of coordination and supramolecular compounds
Mahmudov K.T., Kopylovich M.N., Maharramov A.M., Kurbanova M.M., Gurbanov A.V., Pombeiro A.J.
Coordination Chemistry Reviews, 2014
36.
Click Chemistry: 1,2,3-Triazoles as Pharmacophores
Agalave S.G., Maujan S.R., Pore V.S.
Chemistry - An Asian Journal, 2011
37.
10.1016/j.mencom.2019.11.017_sbref0055b
Haider
Inflammation Cell Signaling, 2014
38.
Medicinal attributes of 1,2,3-triazoles: Current developments
Dheer D., Singh V., Shankar R.
Bioorganic Chemistry, 2017
39.
Biological Properties of 1H-1,2,3- and 2H-1,2,3-Triazoles
de Carvalho da Silva F., Cardoso M.F., Ferreira P.G., Ferreira V.F.
Topics in Heterocyclic Chemistry, 2014
40.
M. J. Orocycl. Chem. FerreiranUS Patent 5064844, 1991.
42.
Synthesis and antifungal activity of 1,2,3-triazole phenylhydrazone derivatives
Dai Z., Chen Y., Zhang M., Li S., Yang T., Shen L., Wang J., Qian S., Zhu H., Ye Y.
Organic and Biomolecular Chemistry, 2015
43.
Synthesis of Novel Glycerol-Derived 1,2,3-Triazoles and Evaluation of Their Fungicide, Phytotoxic and Cytotoxic Activities
Costa A.V., Oliveira M.V., Pinto R.T., Moreira L.C., Gomes E.M., Alves T.D., Pinheiro P.F., Queiroz V.T., Vieira L.F., Teixeira R.R., Júnior W.C.
Molecules, 2017
45.
3-Aryl Substituted Triazole Derivatives as New and Effective Corrosion Inhibitors for Mild Steel in Hydrochloric Acid Solution
Quraishi M.A., Sudheer, Ansari K.R., Ebenso E.E.
International Journal of Electrochemical Science, 2012
46.
10.1016/j.mencom.2019.11.017_sbref0065c
Desai
Int. J. Curr. Microbiol. Appl. Sci., 2015
47.
Corrosion inhibition of copper in aqueous chloride solution by 1H-1,2,3-triazole and 1,2,4-triazole and their combinations: electrochemical, Raman and theoretical studies
Ofoegbu S.U., Galvão T.L., Gomes J.R., Tedim J., Nogueira H.I., Ferreira M.G., Zheludkevich M.L.
Physical Chemistry Chemical Physics, 2017
48.
10.1016/j.mencom.2019.11.017_sbref0065e
Resende
Int. J. Electrochem., 2019
50.
New 1,2,4-triazole-based azo–azomethine dyes. Part II: Synthesis, characterization, electrochemical properties and computational studies
Khanmohammadi H., Erfantalab M., Bayat A., Babaei A., Sohrabi M.
Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2012
52.
10.1016/j.mencom.2019.11.017_bib0075
Willis
Eur. Pat. Appl., 1990
53.
10.1016/j.mencom.2019.11.017_sbref0080a
Chandrasekaran
Click Reactions in Organic Synthesis, 2016
54.
Huisgen’s Cycloaddition Reactions: A Full Perspective
M. Heravi M., Tamimi M., Yahyavi H., Hosseinnejad T.
Current Organic Chemistry, 2015
56.
Muzalevskiy V.M., Mamedzade M.N., Chertkov V.A., Bakulev V.A., Nenajdenko V.G.
Mendeleev Communications, 2018
57.
An effective method for the synthesis of 1,5-disubstituted 4-halo-1H-1,2,3-triazoles from magnesium acetylides
Karsakova I.V., Smirnov A.Y., Baranov M.S.
Chemistry of Heterocyclic Compounds, 2018
58.
10.1016/j.mencom.2019.11.017_bib0085
Novokshonova
Synthesis, 2008
59.
Decisive role of water in efficient noncatalyzed synthesis of polyfunctional 1H-1,2,3-triazoles proceeding from γ-hydroxypropynals
Medvedeva A.S., Demina M.M., Nguyen T.L., Vu T.D., Bulanov D.A., Novokshonov V.V.
Russian Journal of Organic Chemistry, 2013
62.
Spontaneous hydration of the carbonyl group in substituted propynals in aqueous medium
Medvedeva A.S., Mitroshina I.V., Afonin A.V., Chernyshev K.A., Bulanov D.A., Mareev A.V.
Russian Journal of Organic Chemistry, 2013
63.
Synthesis of acetylenic ? -hydroxy aldehydes and their reaction with primary amines
Medvedeva A.S., Safronova L.P., Chichkareva G.G., Voronkov M.G.
Russian Chemical Bulletin, 1976