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Advances in the synthesis of benzimidazolones via rearrangements of benzodiazepinones and quinoxalin(on)es

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Mamedov V. A., Zhukova N. A., Sinyashin O. G. Advances in the synthesis of benzimidazolones via rearrangements of benzodiazepinones and quinoxalin(on)es // Mendeleev Communications. 2016. Vol. 27. No. 1. pp. 1-11.
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Mamedov V. A., Zhukova N. A., Sinyashin O. G. Advances in the synthesis of benzimidazolones via rearrangements of benzodiazepinones and quinoxalin(on)es // Mendeleev Communications. 2016. Vol. 27. No. 1. pp. 1-11.
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TY - JOUR
DO - 10.1016/j.mencom.2017.01.001
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2017.01.001
TI - Advances in the synthesis of benzimidazolones via rearrangements of benzodiazepinones and quinoxalin(on)es
T2 - Mendeleev Communications
AU - Mamedov, Vakhid Abdulla-ogly
AU - Zhukova, Nataliya Anatol'evna
AU - Sinyashin, Oleg Gerol'dovich
PY - 2016
DA - 2016/12/29
PB - Mendeleev Communications
SP - 1-11
IS - 1
VL - 27
ER -
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@article{2016_Mamedov,
author = {Vakhid Abdulla-ogly Mamedov and Nataliya Anatol'evna Zhukova and Oleg Gerol'dovich Sinyashin},
title = {Advances in the synthesis of benzimidazolones via rearrangements of benzodiazepinones and quinoxalin(on)es},
journal = {Mendeleev Communications},
year = {2016},
volume = {27},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2017.01.001},
number = {1},
pages = {1--11},
doi = {10.1016/j.mencom.2017.01.001}
}
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Mamedov, Vakhid Abdulla-ogly, et al. “Advances in the synthesis of benzimidazolones via rearrangements of benzodiazepinones and quinoxalin(on)es.” Mendeleev Communications, vol. 27, no. 1, Dec. 2016, pp. 1-11. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2017.01.001.
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Abstract

The review critically analyzes methods for the preparation of benzimidazolones proceeding via the rearrangements of benzodiazepinones and quinoxalin(on)es, highlights recent advances in the synthesis of bi- and tri-heterocyclic systems with the benzimidazolone moiety, and the advantages and major challenges in their biomedical applications.

References

1.
Potent benzimidazolone-based CGRP receptor antagonists
Theberge C.R., Bednar R.A., Bell I.M., Corcoran H.A., Fay J.F., Hershey J.C., Johnston V.K., Kane S.A., Mosser S., Salvatore C.A., Williams T.M., Zartman C.B., Zhang X., Graham S.L., Vacca J.P., et. al.
Bioorganic and Medicinal Chemistry Letters, 2008
2.
Benzimidazole-2-one: A novel anchoring principle for antagonizing p53-Mdm2
Wang W., Cao H., Wolf S., Camacho-Horvitz M.S., Holak T.A., Dömling A.
Bioorganic and Medicinal Chemistry, 2013
3.
The SAR studies of novel CB2 selective agonists, benzimidazolone derivatives
Omura H., Kawai M., Shima A., Iwata Y., Ito F., Masuda T., Ohta A., Makita N., Omoto K., Sugimoto H., Kikuchi A., Iwata H., Ando K.
Bioorganic and Medicinal Chemistry Letters, 2008
4.
Synthesis and evaluation of N-3 substituted phenoxypropyl piperidine benzimidazol-2-one analogues as NOP receptor agonists with analgesic and sedative properties
Palin R., Bom A., Clark J.K., Evans L., Feilden H., Houghton A.K., Jones P.S., Montgomery B., Weston M.A., Wishart G.
Bioorganic and Medicinal Chemistry, 2007
5.
Structure–activity relationships and CoMFA of N-3 substituted phenoxypropyl piperidine benzimidazol-2-one analogues as NOP receptor agonists with analgesic properties
Palin R., Clark J.K., Evans L., Houghton A.K., Jones P.S., Prosser A., Wishart G., Yoshiizumi K.
Bioorganic and Medicinal Chemistry, 2008
6.
Novel 1,3-dihydro-benzimidazol-2-ones and their analogues as potent non-nucleoside HIV-1 reverse transcriptase inhibitors
Monforte A., Logoteta P., Luca L.D., Iraci N., Ferro S., Maga G., De Clercq E., Pannecouque C., Chimirri A.
Bioorganic and Medicinal Chemistry, 2010
7.
Synthesis and SAR of 1-Hydroxy-1H-benzo[d]imidazol-2(3H)-ones as Inhibitors of d-Amino Acid Oxidase
Berry J.F., Ferraris D.V., Duvall B., Hin N., Rais R., Alt J., Thomas A.G., Rojas C., Hashimoto K., Slusher B.S., Tsukamoto T.
ACS Medicinal Chemistry Letters, 2012
8.
Respiratory syncytial virus fusion inhibitors. Part 3: Water-soluble benzimidazol-2-one derivatives with antiviral activity in vivo
Yu K., Wang X.A., Civiello R.L., Trehan A.K., Pearce B.C., Yin Z., Combrink K.D., Gulgeze H.B., Zhang Y., Kadow K.F., Cianci C.W., Clarke J., Genovesi E.V., Medina I., Lamb L., et. al.
Bioorganic and Medicinal Chemistry Letters, 2006
9.
Identification of triazinoindol-benzimidazolones as nanomolar inhibitors of the Mycobacterium tuberculosis enzyme TDP-6-deoxy-d-xylo-4-hexopyranosid-4-ulose 3,5-epimerase (RmlC)
Sivendran S., Jones V., Sun D., Wang Y., Grzegorzewicz A.E., Scherman M.S., Napper A.D., McCammon J.A., Lee R.E., Diamond S.L., McNeil M.
Bioorganic and Medicinal Chemistry, 2010
10.
Discovery and design of benzimidazolone based inhibitors of p38 MAP kinase
Hammach A., Barbosa A., Gaenzler F.C., Fadra T., Goldberg D., Hao M., Kroe R.R., Liu P., Qian K.C., Ralph M., Sarko C., Soleymanzadeh F., Moss N.
Bioorganic and Medicinal Chemistry Letters, 2006
11.
10.1016/j.mencom.2017.01.001_bib0055
Vora
Der Pharma Chem., 2010
12.
Benzimidazolones: A New Class of Selective Peroxisome Proliferator-Activated Receptor γ (PPARγ) Modulators
Liu W., Lau F., Liu K., Wood H.B., Zhou G., Chen Y., Li Y., Akiyama T.E., Castriota G., Einstein M., Wang C., McCann M.E., Doebber T.W., Wu M., Chang C.H., et. al.
Journal of Medicinal Chemistry, 2011
13.
SAR studies of 6-aryl-1,3-dihydrobenzimidazol-2-ones as progesterone receptor antagonists
Terefenko E.A., Kern J., Fensome A., Wrobel J., Zhu Y., Cohen J., Winneker R., Zhang Z., Zhang P.
Bioorganic and Medicinal Chemistry Letters, 2005
14.
Receptor-based QSAR study for a series of 3,3-disubstituted-5-aryl oxindoles and 6-aryl benzimidazol-2-ones derivatives as progesterone receptor inhibitors
15.
Expeditious Process Improvement for the Synthesis of RWJ-333966
Guillaume M.
Organic Process Research and Development, 2006
16.
Benzimidazolones and indoles as non-thiol farnesyltransferase inhibitors based on tipifarnib scaffold: synthesis and activity
Li Q., Li T., Woods K.W., Gu W., Cohen J., Stoll V.S., Galicia T., Hutchins C., Frost D., Rosenberg S.H., Sham H.L.
Bioorganic and Medicinal Chemistry Letters, 2005
17.
Natural Modulators of Large-Conductance Calcium-Activated Potassium Channels
Nardi Antonio, Calderone Vincenzo, Chericoni Silvio, Morelli Ivano
Planta Medica, 2003
18.
N-Benzylated benzimidazol-2-one derivatives: activators of large-conductance Ca2+-dependent K+ channels
Meanwell N.A., Sit S., Gao J., Boissard C.G., Lum-Ragan J., Dworetzky S.I., Gribkoff V.K.
Bioorganic and Medicinal Chemistry Letters, 1996
24.
Identification of novel, orally bioavailable spirohydantoin CGRP receptor antagonists
Bell I.M., Bednar R.A., Fay J.F., Gallicchio S.N., Hochman J.H., McMasters D.R., Miller-Stein C., Moore E.L., Mosser S.D., Pudvah N.T., Quigley A.G., Salvatore C.A., Stump C.A., Theberge C.R., Wong B.K., et. al.
Bioorganic and Medicinal Chemistry Letters, 2006
25.
Respiratory syncytial virus fusion inhibitors. Part 4: Optimization for oral bioavailability
Yu K., Sin N., Civiello R.L., Wang X.A., Combrink K.D., Gulgeze H.B., Venables B.L., Wright J.J., Dalterio R.A., Zadjura L., Marino A., Dando S., D’Arienzo C., Kadow K.F., Cianci C.W., et. al.
Bioorganic and Medicinal Chemistry Letters, 2007
26.
Synthesis of J-113397, the first potent and selective ORL1 antagonist
Kawamoto H., Nakashima H., Kato T., Arai S., Kamata K., Iwasawa Y.
Tetrahedron, 2001
27.
Lead identification of benzimidazolone and azabenzimidazolone arylsulfonamides as CC-chemokine receptor 4 (CCR4) antagonists
Miah A.H., Abas H., Begg M., Marsh B.J., O’Flynn D.E., Ford A.J., Percy J.M., Procopiou P.A., Richards S.A., Rumley S.
Bioorganic and Medicinal Chemistry, 2014
28.
Hit-to-lead investigation of a series of novel combined dopamine D2 and muscarinic M1 receptor ligands with putative antipsychotic and pro-cognitive potential
Sams A.G., Larsen K., Mikkelsen G.K., Hentzer M., Christoffersen C.T., Jensen K.G., Frederiksen K., Bang-Andersen B.
Bioorganic and Medicinal Chemistry Letters, 2012
29.
10.1016/j.mencom.2017.01.001_bib0145
Cheeseman
Chemistry of Heterocyclic Compounds. Vol. 35. Condensed Pyrazines, 1979
31.
10.1016/j.mencom.2017.01.001_bib0155
Mamedov
Quinoxalines: Synthesis, Reactions, Mechanisms and Structure, 2016
32.
10.1016/j.mencom.2017.01.001_bib0160
Grimmett
Imidazole and Benzimidazole Synthesis, 1997
33.
Recyclization reactions leading to benzimidazoles
Mamedov V.A., Murtazina A.M.
Russian Chemical Reviews, 2011
34.
55. The condensation of o-phenylenediamine with ethyl acetoacetate
Sexton W.A.
Journal of the Chemical Society (Resumed), 1942
35.
Ueber die Einwirkung der Aldehyde auf aromatische Orthodiamine
Hinsberg O., Koller P.
Berichte der deutschen chemischen Gesellschaft, 1896
36.
10.1016/j.mencom.2017.01.001_bib0180
Monti
Gazzetta, 1940
40.
Thermal rearrangement of condensed dihydrodiazepinones
Israel M., Jones L.C., Modest E.J.
Tetrahedron Letters, 1968
43.
Schmidt reaction of some constrained aromatic acids, and related topics
Ruediger E.H., Gandhi S.S., Gibson M.S., Fărcaşiu D., Uncuţa C.
Canadian Journal of Chemistry, 1986
46.
Synthesis of 5(and 6)-nitro-4-methyl-2,3-dihydro-1h-1,5-benzo-2-diazepinones
Kost A.N., Solomko Z.F., Budylin V.A., Semenova T.S.
Chemistry of Heterocyclic Compounds, 1972
48.
Design, synthesis, and cytotoxicity of 4-sulfonamide substituted benzamidobenzimidazolones and an acyl benzimidazolone
Khodarahmi G.A., Chen C.S., Hakimelahi G.H., Tseng C.T., Chern J.W.
Journal of the Iranian Chemical Society, 2005
50.
One-pot microwave assisted synthesis of new 2-alkoxycarbonylmethylene-4-oxo-1,5-benzo-, naphtho-, and pyridodiazepines and assessment of their cytogenetic activity
Eleftheriadis N., Neochoritis C.G., Tsoleridis C.A., Stephanidou-Stephanatou J., Iakovidou-Kritsi Z.
European Journal of Medicinal Chemistry, 2013
53.
Ugi/Aldol Sequence: Expeditious Entry to Several Families of Densely Substituted Nitrogen Heterocycles
Xu Z., De Moliner F., Cappelli A.P., Hulme C.
Angewandte Chemie - International Edition, 2012
58.
Three Questionable Cases in the Chemistry of Quinoxalines and Benzodiazepines in the Way of the Syntheses of Benzimidazoles
Mamedov V.A., Murtazina A.M., Adgamova D.I., Zhukova N.A., Beschastnova T.N., Kharlamov S.V., Rizvanov I.K., Latypov S.K.
Journal of Heterocyclic Chemistry, 2014
59.
Photochemical reactions of azoxy compounds, nitrones, and aromatic amine N-oxides
60.
Photolysis of a quinoxaline-di-N-oxide
Haddadin M.J., Issidorides C.H.
Tetrahedron Letters, 1967
61.
Synthesis and photolysis of some substituted quinoxaline di-N-oxides
Haddadin M.J., Agopian G., Issidorides C.H.
Journal of Organic Chemistry, 1971
62.
Photolysis of Some Quinoxaline-1,4-dioxides. A Method of Structural Assignment
63.
The complex photo-rearrangement of a heterocyclic N-oxide: Kinetics from picoseconds to minutes
Cordes T., Regner N., Heinz B., Borysova E., Ryseck G., Gilch P.
Journal of Photochemistry and Photobiology A: Chemistry, 2009
64.
Photolysis of some quinoxaline-1,4-dioxides
Jarrar A.A., Fataftah Z.A.
Tetrahedron, 1977
65.
Quinoxaline derivatives. X. Novel rearrangement of certain quinoxaline N-oxides to 6-benzimidazolinones
Ahmad Y., Habib M.S., Mohammady A., Bakhtiari B., Shamsi S.A.
Journal of Organic Chemistry, 1968
68.
A new facile, efficient synthesis and structure peculiarity of quinoxaline derivatives with two benzimidazole fragments
Mamedov V.A., Zhukova N.A., Syakaev V.V., Gubaidullin A.T., Beschastnova T.N., Adgamova D.I., Samigullina A.I., Latypov S.K.
Tetrahedron, 2013
72.
Quinoxaline-benzimidazole rearrangement in the synthesis of benzimidazole-based podands
Mamedov V.A., Kalinin A.A., Gubaidullin A.T., Gorbunova E.A., Litvinov I.A.
Russian Journal of Organic Chemistry, 2006
73.
An efficient metal-free synthesis of 2-(pyrazin-2-yl)benzimidazoles from quinoxalinones and diaminomaleonitrile via a novel rearrangement
Mamedov V.A., Zhukova N.A., Beschastnova T.N., Zakirova E.I., Kadyrova S.F., Mironova E.V., Nikonova A.G., Latypov S.K., Litvinov I.A.
Tetrahedron Letters, 2012
74.
A simple and efficient method for the synthesis of highly substituted imidazoles using 3-aroylquinoxalin-2(1H)-ones
Mamedov V.A., Zhukova N.A., Beschastnova T.N., Gubaidullin A.T., Rakov D.V., Rizvanov I.K.
Tetrahedron Letters, 2011
75.
Acid-catalyzed rearrangement of 3-(β-2-aminostyryl)quinoxalin-2(1H)ones—a new and efficient method for the synthesis of 2-benzimidazol-2-ylquinolines
Mamedov V.A., Saifina D.F., Gubaidullin A.T., Ganieva V.R., Kadyrova S.F., Rakov D.V., Rizvanov I.K., Sinyashin O.G.
Tetrahedron Letters, 2010
77.
Benzimidazoles and related heterocycles
Mamedov V.A., Murtazina A.M., Gubaidullin A.T., Khafizova E.A., Rizvanov I.K., Litvinov I.A.
Russian Chemical Bulletin, 2010
79.
Ueber Chinoxaline
Hinsberg O.
Berichte der deutschen chemischen Gesellschaft, 1884
80.
Phenylhydrazin als Reagens auf Aldehyde und Ketone
Fischer E.
Berichte der deutschen chemischen Gesellschaft, 1884
82.
Ueber die Constitution des Lophins und verwandter Verbindungen
Radziszewski B.
Berichte der deutschen chemischen Gesellschaft, 1882
83.
Constitution des Lophins und des Amarins
Japp F.R., Robinson H.H.
Berichte der deutschen chemischen Gesellschaft, 1882
84.
Tautomerie in der Pyridin-Reihe
Tschitschibabin A.E.
Berichte der deutschen chemischen Gesellschaft (A and B Series), 1927
85.
Synthese von Pyrrolderivaten
Knorr L.
Berichte der deutschen chemischen Gesellschaft, 1884
87.
10.1016/j.mencom.2017.01.001_bib0435
Hassner
Organic Syntheses Based on Name Reactions, 2012
88.
10.1016/j.mencom.2017.01.001_bib0440
Mamedov
2013
89.
Reaction for the Synthesis of Benzimidazol-2-ones, Imidazo[5,4-b]-, and Imidazo[4,5-c]pyridin-2-ones via the Rearrangement of Quinoxalin-2-ones and Their Aza Analogues When Exposed to Enamines
Mamedov V.A., Zhukova N.A., Zamaletdinova A.I., Beschastnova T.N., Kadyrova M.S., Rizvanov I.K., Syakaev V.V., Latypov S.K.
Journal of Organic Chemistry, 2014
92.
Direct Catalytic Asymmetric Michael Reaction of Hydroxyketones:  Asymmetric Zn Catalysis with a Et2Zn/Linked-BINOL Complex
Harada S., Kumagai N., Kinoshita T., Matsunaga S., Shibasaki M.
Journal of the American Chemical Society, 2003
94.
Geminal bond participation in Alder ene reaction
Naruse Y., Suzuki T., Inagaki S.
Tetrahedron Letters, 2005
95.
Cobalt-Catalyzed Alder–Ene Reaction
Hilt G., Treutwein J.
Angewandte Chemie - International Edition, 2007
97.
Alkaloid synthesis via intramolecular ene reactions. 1. Application to (.+-.)-crinane
Keck G.E., Webb R.R.
Journal of the American Chemical Society, 1981
100.
D. F. Saifina, PhD Thesis, 2009.
101.
Rearrangement of Quinoxalin-2-ones When Exposed to Enamines Generated in Situ from Ketones and Ammonium Acetate: Method for the Synthesis of 1-(Pyrrolyl)benzimidazolones
Mamedov V.A., Zhukova N.A., Beschastnova T.N., Syakaev V.V., Krivolapov D.B., Mironova E.V., Zamaletdinova A.I., Rizvanov I.K., Latypov S.K.
Journal of Organic Chemistry, 2015
102.
10.1016/j.mencom.2017.01.001_bib0510
Comprehensive Organic Name Reactions and Reagents, 2009
103.
10.1016/j.mencom.2017.01.001_bib0515
Smith
March's Advanced Organic Chemistry, 2001
104.
10.1016/j.mencom.2017.01.001_bib0520
The Chemistry of Enamines, 1994