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A convenient synthesis of 3-aryl-5-methylidene-2-thiohydantoins

Maxim Evgenievich Kukushkin
Nikita Aleksandrovich Karpov 1
Nikita Aleksandrovich Karpov
Dmitry Evgenievich Shybanov 1
Dmitry Evgenievich Shybanov
Nikolai Vasil'evich Zyk 1
Nikolai Vasil'evich Zyk
Published 2022-01-03
CommunicationVolume 32, Issue 1, 126-128
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Kukushkin M. E. et al. A convenient synthesis of 3-aryl-5-methylidene-2-thiohydantoins // Mendeleev Communications. 2022. Vol. 32. No. 1. pp. 126-128.
GOST all authors (up to 50) Copy
Kukushkin M. E., Karpov N. A., Shybanov D. E., Zyk N. V., Beloglazkina E. K. A convenient synthesis of 3-aryl-5-methylidene-2-thiohydantoins // Mendeleev Communications. 2022. Vol. 32. No. 1. pp. 126-128.
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TY - JOUR
DO - 10.1016/j.mencom.2022.01.041
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.01.041
TI - A convenient synthesis of 3-aryl-5-methylidene-2-thiohydantoins
T2 - Mendeleev Communications
AU - Kukushkin, Maxim Evgenievich
AU - Karpov, Nikita Aleksandrovich
AU - Shybanov, Dmitry Evgenievich
AU - Zyk, Nikolai Vasil'evich
AU - Beloglazkina, Elena Kimovna
PY - 2022
DA - 2022/01/03
PB - Mendeleev Communications
SP - 126-128
IS - 1
VL - 32
ER -
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@article{2022_Kukushkin,
author = {Maxim Evgenievich Kukushkin and Nikita Aleksandrovich Karpov and Dmitry Evgenievich Shybanov and Nikolai Vasil'evich Zyk and Elena Kimovna Beloglazkina},
title = {A convenient synthesis of 3-aryl-5-methylidene-2-thiohydantoins},
journal = {Mendeleev Communications},
year = {2022},
volume = {32},
publisher = {Mendeleev Communications},
month = {Jan},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.01.041},
number = {1},
pages = {126--128},
doi = {10.1016/j.mencom.2022.01.041}
}
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Kukushkin, Maxim Evgenievich, et al. “A convenient synthesis of 3-aryl-5-methylidene-2-thiohydantoins.” Mendeleev Communications, vol. 32, no. 1, Jan. 2022, pp. 126-128. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.01.041.

Keywords

2-thiohydantoins
amino acids
exocyclic C=C bond
heterocyclization
isothiocyanates

Abstract

3-Aryl-5-methylidene-2-thiohydantoins were constructed in one-pot reaction of aryl isothiocyanates and 3-morpholino- alanine in alkaline medium with the subsequent treatment with boiling hydrochloric acid.

References

1.
Recent applications of hydantoin and thiohydantoin in medicinal chemistry
Cho S., Kim S., Shin D.
European Journal of Medicinal Chemistry, 2019
3.
10.1016/j.mencom.2022.01.041_b0015
Hahn
J. Am. Chem. Soc., 1927
4.
10.1016/j.mencom.2022.01.041_b0020
McKee
J. Am. Chem. Soc., 2020
6.
A new method for the synthesis of 5-bromo(aryl)methylene-substituted hydantoins
Antipin R.L., Beloglazkina E.K., Magouga A.G., Chernysheva A.N., Zyk N.V.
Chemistry of Heterocyclic Compounds, 2008
7.
SITE SELECTIVITY AND REGIOCHEMISTRY OF NITRILIMINES. CYCLOADDITIONS TO 1,3-DIPHENYL-2-THIONO-4-IMIDAZOLIDINONE AND ITS 5-PHENYLMETHYLENE DERIVATIVES
Hassaneen H.M., Daboun H.A., Abdelhadi H.A., Abdel-reheim N.A.
Phosphorus, Sulfur and Silicon and the Related Elements, 1995
8.
First example of [3+2] cycloaddition of azomethine ylides to 5-methylidene-3-phenylhydantoin
Kukushkin M.E., Kondratyeva A.A., Zyk N.V., Majouga A.G., Beloglazkina E.K.
Russian Chemical Bulletin, 2019
9.
Shybanov D.E., Kukushkin M.E., Tafeenko V.A., Zyk N.V., Grishin Y.K., Roznyatovsky V.A., Beloglazkina E.K.
Mendeleev Communications, 2021
10.
An Improved Protocol for Synthesis of 3-Substituted 5-Arylidene-2-thiohydantoins: Two-step Procedure Alternative to Classical Methods
Kuznetsova O.Y., Antipin R.L., Udina A.V., Krasnovskaya O.O., Beloglazkina E.K., Terenin V.I., Koteliansky V.E., Zyk N.V., Majouga A.G.
Journal of Heterocyclic Chemistry, 2015
11.
NEW EFFICIENT SYNTHESIS OF 2-ALKYLTHIO-5-BENZYLJDENE-4H-IMIDAZOLIN-4-ONES
Ding M., Sun Y., Liu X., Liu Z.
Organic Preparations and Procedures International, 2003
13.
Synthesis and cytotoxicity of oxindoles dispiro derivatives with thiohydantoin and adamantane fragments
Kukushkin M.E., Skvortsov D.A., Kalinina M.A., Tafeenko V.A., Burmistrov V.V., Butov G.M., Zyk N.V., Majouga A.G., Beloglazkina E.K.
Phosphorus, Sulfur and Silicon and the Related Elements, 2020
14.
Isatin derivatives with activity against apoptosis-resistant cancer cells
Evdokimov N.M., Magedov I.V., McBrayer D., Kornienko A.
Bioorganic and Medicinal Chemistry Letters, 2016
18.
Synthesis of new 5-substituted hydantoins and symmetrical twin-drug type hydantoin derivatives.
Fujisaki F., Aki H., Naito A., Fukami E., Kashige N., Miake F., Sumoto K.
Chemical and Pharmaceutical Bulletin, 2014
19.
Synthesis of 5-Chloromethylene Hydantoins and Thiohydantoins
20.
Preparation and chemical properties of 5-dialkylaminomethylhydantoins and 2-thio-analogues.
Fujisaki F., Shoji K., Sumoto K.
Chemical and Pharmaceutical Bulletin, 2009
21.
Preparation of diethyl formamidomalonate
Galun A.B.
Journal of Chemical & Engineering Data, 1976
22.
Synthesis of .BETA.-(sec-Amino)alanines.
ABE N., FUJISAKI F., SUMOTO K.
Chemical and Pharmaceutical Bulletin, 2011
23.
Edman P., Dynesen E., Webb M., Rottenberg M.
Acta Chemica Scandinavica, 1950
24.
Effect of pH of a medium on the direction of reactions of isothiocyanates with amino acids
Yakusheva A.V., Galibeev S.S., Spiridonova R.R., Samuilov Y.D., Kochnev A.M.
Polymer Science - Series B, 2008