Abstract
Glycolurils --- tetrahydroimidazo[4,5-$d$]imidazole-2,5($1H$, $3H$)-diones --- have found widespread applications in various fields of science and technology. Among them, there are pharmacologically active compounds (antibacterial, nootropic, neurotropic agents, \textit{etc.}), explosives, gelators, \textit{etc}. They are used as building blocks in supramolecular chemistry. Therefore, the development of new methods for the synthesis of glycolurils and their analogues has constantly attracted the attention of researchers. In this review, we analyze various approaches to the synthesis of glycolurils and their analogues. The review covers both classical reactions of ureas and related compounds with $\alpha$-dicarbonyl compounds or with 4,5-dihydroxyimidazolidin-2-ones (-thiones) and their imino analogues and new original reactions of 4,5-dihydroxyimidazolidin-2-ones (-thiones), imidazolinones and their bicyclic analogues with ureas and KNCS in the presence of acids, condensations of 1,4-disubstituted 1,4-diaza-1,3-dienes with isocyanic and/or isothiocyanic acids or isocyanates, triazine ring contraction in imidazotriazines to give the imidazolidine ring, and transformations of urazoles.
The bibliography includes 129 references.
Funders
Russian Science Foundation
17-73-10415
References
1.
rcr_87_1_89bib1
2006
2.
rcr_87_1_89bib2
2001
3.
rcr_87_1_89bib3
2008
4.
Ryzhkina Irina Sergeevna, Kiseleva Yuliya Vasil'evna, Mishina Olga Aleksandrovna, Timosheva Alina Petrovna, Sergeeva Svetlana Yuryevna, Kravchenko Angelina Nikolaevna, Konovalov Aleksandr Ivanovich
Mendeleev Communications ,
2013
5.
Berlyand A.S., Lebedev O.V., Prokopov A.A.
Pharmaceutical Chemistry Journal ,
2013
6.
![Neuroprotective activity of (+)-(S)-2-[(1S,5R)-(3,7-dioxo-2,4,6,8- tetraazabicyclo[3.3.0]oct-2-yl)]-4-methylthiobutanoic acid](https://rcr.colab.ws/storage/images/resized/oZgeErrVFhuDksyqFURLvYS1wtVSBWczh001igGo_small_thumb.webp)
Kravchenko A.N., Baranov V.V., Anikina L.V., Vikharev Y.B., Bushmarinov I.S., Nelyubina Y.V.
Russian Journal of Bioorganic Chemistry ,
2012
7.
Cui K., Xu G., Xu Z., Wang P., Xue M., Meng Z., Li J., Wang B., Ge Z., Qin G.
Propellants, Explosives, Pyrotechnics ,
2014
8.
Zharkov M.N., Kuchurov I.V., Fomenkov I.V., Zlotin S.G., Tartakovsky V.A.
Mendeleev Communications ,
2015
9.
Sal’keeva L.K., Bakibaev A.A., Khasenova G.T., Taishibekova Y.K., Sugralina L.M., Minaeva Y.V., Sal’keeva A.K.
Russian Journal of Applied Chemistry ,
2016
10.
rcr_87_1_89bib10
Kölbel
2001
11.
Tiefenbacher K., Dube H., Ajami D., Rebek, J.
Chemical Communications ,
2011
12.
Lagona J., Mukhopadhyay P., Chakrabarti S., Isaacs L.
Angewandte Chemie - International Edition ,
2005
13.
![Bambus[n]urils: a New Family of Macrocyclic Anion Receptors](https://rcr.colab.ws/storage/images/resized/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_small_thumb.webp)
Havel V., Svec J., Wimmerova M., Dusek M., Pojarova M., Sindelar V.
Organic Letters ,
2011
14.
Singh M., Solel E., Keinan E., Reany O.
Chemistry - A European Journal ,
2016
15.
Elemans J.A., Rowan A.E., Nolte R.J.
Industrial & Engineering Chemistry Research ,
2000
16.
rcr_87_1_89bib16
She
2008
17.
![Glycoluril derivatives form hydrogen bonded tapes rather than cucurbit[n]uril congeners](https://rcr.colab.ws/storage/images/resized/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_small_thumb.webp)
Wu A., Fettinger J.C., Isaacs L.
Tetrahedron ,
2002
18.
She N., Gao M., Meng X., Yang G., Elemans J.A., Wu A., Isaacs L.
Journal of the American Chemical Society ,
2009
19.
Singh M., Solel E., Keinan E., Reany O.
Chemistry - A European Journal ,
2014
20.
Rowan A.E., Elemans J.A., Nolte R.J.
Accounts of Chemical Research ,
1999
21.
Yahyaei S., Vessally E., Massoumi B., Rafati M.
Phosphorus, Sulfur and Silicon and the Related Elements ,
2014
22.
rcr_87_1_89bib22
Singh
2014
23.
Khaksar S., Vahdat S.M., Tajbakhsh M., Jahani F., Heydari A.
Tetrahedron Letters ,
2010
24.
rcr_87_1_89bib24
Cao
2009
25.
Kam K., Rahimizadeh M., McDonald R.S., Harrison P.H., Chen H., Jenkins S.I., Pedrech A.
Canadian Journal of Chemistry ,
2005
26.
Cow C.N., Harrison P.H.
Journal of Organic Chemistry ,
1997
27.
Kravchenko Angelina Nikolaevna, Chikunov Il'ya Evgen'evich, Gazieva Galina Anatol'evna, Makhova Nina Nikolaevna
Mendeleev Communications ,
2016
28.
Gazieva Galina Anatol'evna, Vikharev Yurii Borisovich, Anikina Lada Vladimirovna, Karpova Tatyana B, Kravchenko Angelina Nikolaevna, Permyakov Evgenii Aleksandrovich, Svitanko Igor
Mendeleev Communications ,
2013
29.
Gazieva G.A., Anikina L.V., Pukhov S.A., Karpova T.B., Nelyubina Y.V., Kravchenko A.N.
Molecular Diversity ,
2016
30.
Gazieva G.A., Anikina L.V., Nechaeva T.V., Pukhov S.A., Karpova T.B., Popkov S.V., Nelyubina Y.V., Kolotyrkina N.G., Kravchenko A.N.
European Journal of Medicinal Chemistry ,
2017
31.
rcr_87_1_89bib31
1999
32.
Sal’keeva L.K., Röschenthaler G.-., Bakibaev A.A., Voitiček P., Shibaeva A.K., Taishibekova E.K., Zhortarova A.A., Sugralina L.M.
Russian Journal of General Chemistry ,
2015
33.
Wang R., Guo Y., Sa R., Shreeve J.
Chemistry - A European Journal ,
2010
34.
Hu B., Jin X., Jia H., Liu Z., Lv C.
Australian Journal of Chemistry ,
2014
35.
rcr_87_1_89bib35
Petersen
1973
36.
Bakibaev A.A., Akhmedzhanov R.R., Yagovkin A.Y., Novozheeva T.P., Filimonov V.D., Saratikov A.S.
Pharmaceutical Chemistry Journal ,
1993
37.
Micheletti G., Delpivo C., Baccolini G.
Green Chemistry Letters and Reviews ,
2012
38.
MOBINIKHALEDI A., AMIRI A.K.
Journal of Chemical Sciences ,
2013
39.
rcr_87_1_89bib39
2004
40.
rcr_87_1_89bib40
2012
41.
Jansen K., Wego A., Buschmann H., Schollmeyer E., Döpp D.
Designed Monomers and Polymers ,
2003
42.
![A New and Efficient Method for the Preparation of 2,4,6,8-Tetraazabicyclo[3.3.0]octane-3,7-diones (Glycolurils) Catalyzed by Keggin, Wells-Dawson, and Preyssler Heteropolyoxometalates, Effect of Structure on the Reactivity](https://rcr.colab.ws/storage/images/resized/doUaFUZdxUEQjLi1TwZjGHi8HXYNWWSk04dSC6Xh_small_thumb.webp)
Tayebee R., Esmaeil R., Behrooz M.
Letters in Organic Chemistry ,
2012
43.
Vessally E., Esrafili M.D., Alimadadi Z., Rouhani M.
Green Chemistry Letters and Reviews ,
2014
44.
Mandadapu V., Wu F., Day A.I.
Organic Letters ,
2014
45.
Azam A., Chawla H.M., Pandey S.
Tetrahedron Letters ,
2010
46.
Shin M., Kim M.H., Ha T., Jeon J., Chung K., Kim J.S., Kim Y.G.
Tetrahedron ,
2014
47.
Li J., Liu X., Sun M.
Ultrasonics Sonochemistry ,
2010
48.
![Synthesis and Crystal Structure of 10-(4-Nitrobenzyl)-3,7,9,11-Tetraoxo-2,4,6,8,10-Pentaaza[3.3.3]Propellane](https://rcr.colab.ws/storage/images/resized/ruydfaB80LDjlkYqsfOeUAZohOIODyq7bQzis5O7_small_thumb.webp)
Yang D., Fu L., Li J., Zhang Q., Shi D.
Journal of Chemical Research ,
2016
49.
Rezaei-Seresht E., Hokmabadi F.
Tetrahedron Letters ,
2010
50.
Creaven B.S., Gallagher J.F., McDonagh J.P., McGinley J., Murray B.A., Whelan G.S.
Tetrahedron ,
2004
51.
Lin J., Zhang Y., Zhang J., Xue S., Zhu Q., Tao Z.
Journal of Molecular Structure ,
2008
52.
Vinciguerra B., Cao L., Cannon J.R., Zavalij P.Y., Fenselau C., Isaacs L.
Journal of the American Chemical Society ,
2012
53.
Wu F., Mandadapu V., Day A.I.
Tetrahedron ,
2013
54.
Azaryan L.V., Mndzhoyan O.L., Avetisyan S.A., Akopyan N.E., Dzhagatspanyan I.A., Akopyan A.G.
Pharmaceutical Chemistry Journal ,
1983
55.
rcr_87_1_89bib55
Bakibaev
Zh. Org. Khim. ,
1988
56.
rcr_87_1_89bib56
Bakibaev
Zh. Org. Khim. ,
1994
57.
Gompper R., Nöth H., Rattay W., Schwarzensteiner M., Spes P., Wagner H.
1987
58.
Kravchenko A.N., Chikunov I.E., Lyssenko K.A., Baranov V.V.
Chemistry of Heterocyclic Compounds ,
2014
59.
Barsegyan Y.A., Baranov V.V., Kravchenko A.N.
Chemistry of Heterocyclic Compounds ,
2017
60.
Broan C.J., Butler A.R., Reed D., Sadler I.H.
Journal of the Chemical Society Perkin Transactions 2 ,
1989
61.
Witt D., Lagona J., Damkaci F., Fettinger J.C., Isaacs L.
Organic Letters ,
2000
62.
rcr_87_1_89bib62
Hu
2009
63.
Gautam S., Ketcham R., Nematollahi J.
Synthetic Communications ,
1979
64.
Kravchenko A.N., Sigachev A.S., Maksareva E.Y., Gazieva G.A., Trunova N.S., Lozhkin B.V., Pivina T.S., Il’in M.M., Lyssenko K.A., Nelyubina Y.V., Davankov V.A., Lebedev O.V., Makhova N.N., Tartakovsky V.A.
Russian Chemical Bulletin ,
2005
65.
Butler A.R., Hussain I.
Journal of the Chemical Society Perkin Transactions 2 ,
1981
66.
67.
Kravchenko A.N., Baranov V.V., Gazieva G.A., Chikunov I.E., Nelyubina Y.V.
Russian Chemical Bulletin ,
2014
68.
rcr_87_1_89bib68
Kostyanovsky
1998
69.
rcr_87_1_89bib69
Kostyanovsky
2001
70.
Stancl M., Necas M., Taraba J., Sindelar V.
Journal of Organic Chemistry ,
2008
71.
Koppes W.M., Chaykovsky M., Adolph H.G., Gilardi R., George C.
Journal of Organic Chemistry ,
1987
72.
Gazieva G.A., Lysenko K.A., Kravchenko A.N., Lebedev O.V.
Russian Journal of Organic Chemistry ,
2007
73.
Grillon E., Gallo R., Pierrot M., Boileau J., Wimmer E.
Tetrahedron Letters ,
1988
74.
Saloutina L.V., Zapevalov A.Y., Slepukhin P.A., Kodess M.I., Saloutin V.I., Chupakhin O.N.
Chemistry of Heterocyclic Compounds ,
2014
75.
Eres'ko V.A., Epishina L.V., Lebedev O.V., Khmel'nitskii L.I., Novikov S.S., Yakubovskii E.A.
Russian Chemical Bulletin ,
1980
76.
Broan C.J., Butler A.R.
Journal of the Chemical Society Perkin Transactions 2 ,
1991
77.
rcr_87_1_89bib77
Terpigorev
Russ. J. Org. Chem. ,
1998
78.
rcr_87_1_89bib78
Chegaev
2001
79.
Kravchenko A.N., Maksareva E.Y., Belyakov P.A., Sigachev A.S., Chegaev K.Y., Lyssenko K.A., Lebedev O.V., Makhova N.N.
Russian Chemical Bulletin ,
2003
80.
Kravchenko A.N., Lyssenko K.A., Chikunov I.E., Belyakov P.A., Il’in M.M., Baranov V.V., Nelyubina Y.V., Davankov V.A., Pivina T.S., Makhova N.N., Antipin M.Y.
Russian Chemical Bulletin ,
2009
81.
Kravchenko A.N., Chikunov I.E.
Russian Chemical Reviews ,
2006
82.
Kravchenko A.N., Sigachev A.S., Belyakov P.A., Ilyin M.M., Lyssenko K.A., Davankov V.A., Lebedev O.V., Makhova N.N., Tartakovsky V.A.
Russian Chemical Bulletin ,
2009
83.
rcr_87_1_89bib83
Lyssenko
2004
84.
Gazieva G.A., Lozhkin P.V., Baranov V.V., Nelyubina Y.V., Kravchenko A.N., Makhova N.N.
Russian Chemical Bulletin ,
2009
85.
Gazieva G.A., Lozhkin P.V., Baranov V.V., Kravchenko A.N., Makhova N.N.
Russian Chemical Bulletin ,
2010
86.
rcr_87_1_89bib86
Chikunov
2005
87.
rcr_87_1_89bib87
Kravchenko
2003
88.
rcr_87_1_89bib88
Chikunov
2004
89.
Nelyubina Y., Baranov V., Antonova M., Kolotyrkina N., Kravchenko A.
Synlett ,
2017
90.
rcr_87_1_89bib90
Correia
Synthesis ,
2016
91.
Svec J., Dusek M., Fejfarova K., Stacko P., Klán P., Kaifer A.E., Li W., Hudeckova E., Sindelar V.
Chemistry - A European Journal ,
2011
92.
Rivollier J., Thuéry P., Heck M.
Organic Letters ,
2013
93.
Yawer M.A., Havel V., Sindelar V.
Angewandte Chemie - International Edition ,
2014
94.
Vasilevskii Sergei Vitalyevich, Nelyubina Yulia Vladimirovna, Kravchenko Angelina Nikolaevna
Mendeleev Communications ,
2009
95.
rcr_87_1_89bib95
Sigachev
2003
96.
Sigachev A.S., Kravchenko A.N., Belyakov P.A., Lebedev O.V., Makhova N.N.
Russian Chemical Bulletin ,
2006
97.
Gazieva G.A., Kravchenko A.N.
Journal of Heterocyclic Chemistry ,
2014
98.
Nelyubina Y., Gazieva G., Karpova T., Nechaeva T., Zanin I., Kravchenko A.
Synlett ,
2017
99.
Baranov Vladimir Vladimirovich, Antonova Maria Mikhailovna, Nelyubina Yulia Vladimirovna, Kolotyrkina Natal'ya Georgievna, Zanin Igor Evgenievich, Kravchenko Angelina Nikolaevna, Makhova Nina Nikolaevna
Mendeleev Communications ,
2014
100.
Antonova M.M., Baranov V.V., Nelyubina Y.V., Kravchenko A.N.
Chemistry of Heterocyclic Compounds ,
2014
101.
Kravchenko A.N., Gazieva G.A., Sigachev A.S., Maksareva E.Y., Lyssenko K.A., Makhova N.N.
Russian Chemical Bulletin ,
2007
102.
rcr_87_1_89bib102
Kravchenko
2000
103.
Gazieva G.A., Baranov V.V., Kravchenko A.N.
Russian Chemical Bulletin ,
2010
104.
Baranov V.V., Nelyubina Y.V., Kravchenko A.N., Makhova N.N.
Russian Chemical Bulletin ,
2010
105.
Gazieva G.A., Baranov V.V., Kravchenko A.N., Makhova N.N.
Russian Journal of Organic Chemistry ,
2011
106.
Baranov V.V., Gazieva G.A., Nelyubina Y.V., Kravchenko A.N., Makhova N.N.
Russian Journal of Organic Chemistry ,
2011
107.
Baranov Vladimir Vladimirovich, Kravchenko Angelina Nikolaevna, Belyakov Pavel Alekseevich, Makhova Nina Nikolaevna
Mendeleev Communications ,
2008
108.
Ivanov E.V., Batov D.V., Baranov V.V., Kravchenko A.N.
Thermochimica Acta ,
2016
109.
Gazieva G.A., Kravchenko A.N., Lyssenko K.A., Gaziev R.G., Lebedev O.V., Makhova N.N.
Russian Chemical Bulletin ,
2008
110.
rcr_87_1_89bib110
Gazieva
2000
111.
Gazieva G.A., Kravchenko A.N., Lebedev O.V., Abelentsev V.I.
Pharmaceutical Chemistry Journal ,
2001
112.
rcr_87_1_89bib112
Gazieva
2001
113.
New access to thioglycolurils by condensation of 4,5-dihydroxyimidazolidin-2-ones(thiones) with HSCN
Baranov V.V., Nelyubina Y.V., Kravchenko A.N., Kolotyrkina N.G., Biriukova K.A.
Tetrahedron Letters ,
2015
114.
Maligres P.E., Waters M.S., Weissman S.A., McWilliams J.C., Lewis S., Cowen J., Reamer R.A., Volante R.P., Reider P.J., Askin D.
Journal of Heterocyclic Chemistry ,
2003
115.
Baranov Vladimir Vladimirovich, Kravchenko Angelina Nikolaevna, Nelyubina Yulia Vladimirovna
Mendeleev Communications ,
2014
116.
Nelyubina Y., Baranov V., Kravchenko A., Antonova M.
Synlett ,
2015
117.
Baranov V.V., Antonova M.M., Karnoukhova V.A., Kravchenko A.N.
Arkivoc ,
2017
118.
![Synthesis of Imdazo[4,5-d]imidazole-2,5-dithiones by Crisscross Addition Reaction of 1,4-Diaza-1,3-dienes to Isothiocyanatorimethylsilane](https://rcr.colab.ws/storage/images/resized/SovkqI6gX6to8o5XBnS9RNxEOYVicn7hatkMzrvl_small_thumb.webp)
Takahashi M., Miyadai S.
Heterocycles ,
1990
119.
Verner J., Taraba J., Potáček M.
Tetrahedron Letters ,
2002
120.
![[Reaction of conjugated systems containing nitrogen. IV. Reaction of conjugated 1,2-diimines with isocyanates].](https://rcr.colab.ws/storage/images/resized/KBGMujzjwr0rGFxg8Kz0qvYdFHkcBo5w0GTtfiiU_small_thumb.webp)
SAKAMOTO M., TOMIMATSU Y., MIYAZAWA K., TOKORO K.
Yakugaku Zasshi ,
2017
121.
rcr_87_1_89bib121
Brehme
2003
122.
Kravchenko Angelina Nikolaevna, Gazieva Galina Anatol'evna, Vasilevskii Sergei Vitalyevich, Belyakov Pavel Alekseevich, Nelyubina Yulia Vladimirovna
Mendeleev Communications ,
2012
123.
Gazieva G., Poluboyarov P., Popov L., Kolotyrkina N., Kravchenko A., Makhova N.
Synthesis ,
2012
124.
Gazieva G.A., Karpova T.B., Popov L.D., Nelyubina Y.V., Kravchenko A.N.
Journal of Heterocyclic Chemistry ,
2014
125.
Gazieva G.A., Karpova T.B., Nechaeva T.V., Kravchenko A.N.
Russian Chemical Bulletin ,
2016
126.
Gazieva G.A., Serkov S.A., Sigay N.V., Kostikova N.N., Popov L.D., Kravchenko A.N.
Arkivoc ,
2017
127.
Tanaka S., Seguchi K., Itoh K., Sera A.
Journal of the Chemical Society Perkin Transactions 1 ,
1994
128.
Seguchi K., Tanaka S., Sera A.
Heterocycles ,
1994
129.
Saloutina L.V., Zapevalov A.Y., Slepukhin P.A., Kodess M.I., Saloutin V.I., Chupakhin O.N.
Russian Chemical Bulletin ,
2016