Abstract:
The 1,3-dipolar cycloaddition of azido-1,2,5-oxadiazoles (azidofurazans) to dicarbonyl compounds was studied, and a new procedure for the synthesis of 4-R-3-(4-R1-5-R2-1,2,3-triazol-1-yl)-1,2,5-oxadiazoles was proposed.
Document Type:
Article
Language: English
Citation:
L. V. Batog, V. Yu. Rozhkov, M. I. Struchkova, “Azido-1,2,5-oxadiazoles in reactions with 1,3-dicarbonyl compounds”, Mendeleev Commun., 12:4 (2002), 159–162
Linking options:
https://www.mathnet.ru/eng/mendc4142
https://www.mathnet.ru/eng/mendc/v12/i4/p159
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V. A. Bakulev, Yu. M. Shafran, N. A. Beliaev, T. V. Beryozkina, N. N. Volkova, M. N. Joy, Z. Fan, “Heterocyclic azides: advances in their chemistry”, Russian Chem. Reviews, 91:7 (2022), RCR5042
Alexey M. Starosotnikov, Vladislav V. Nikol'skiy, Anastasiya N. Borodulya, Vadim V. Kachala, Maxim A. Bastrakov, Vitaly N. Solkan, Svyatoslav A. Shevelev, “Synthesis and Functionalization of 5,7‐Dinitroquinoline and Its N‐Oxide”, Asian J Org Chem, 5:5 (2016), 685
L. L. Fershtat, S. S. Ashirbaev, A. S. Kulikov, V. V. Kachala, N. N. Makhova, “Ionic liquid-mediated synthesis of (1H-1,2,3-triazol-1-yl)furoxans by [3 + 2] cycloaddition of azidofuroxans to acetylenes”, Mendeleev Commun., 25:4 (2015), 257–259
A. S. Kulikov, M. A. Epishina, L. V. Batog, V. Yu. Rozhkov, N. N. Makhova, L. D. Konyushkin, M. N. Semenova, V. V. Semenov, “Synthesis and antineoplastic properties of (1H-1,2,3-triazol-1-yl)furazans”, Russ Chem Bull, 62:3 (2013), 836
L. V. Batog, V. Yu. Rozhkov, M. I. Struchkova, A. S. Kulikov, N. N. Makhova, “Synthesis of N,N′-bis[4-(1H-1,2,3-triazol-1-yl)furazan-3-yl]-methylenediamine derivatives”, Russ Chem Bull, 62:6 (2013), 1391
Yury A. Rozin, Johann Leban, Wim Dehaen, Valentine G. Nenajdenko, Vasiliy M. Muzalevskiy, Oleg S. Eltsov, Vasiliy A. Bakulev, “Regioselective synthesis of 5-trifluoromethyl-1,2,3-triazoles via CF3-directed cyclization of 1-trifluoromethyl-1,3-dicarbonyl compounds with azides”, Tetrahedron, 68:2 (2012), 614
Yuri Shafran, Yuri Rozin, Tetyana Beryozkina, Sergei Zhidovinov, Oleg Eltsov, Julia Subbotina, Johann Leban, Rashida Novikova, Vasiliy Bakulev, “Self condensation of enamines mediated by acetylation. A novel approach to 1-(azol-5-yl)-(1E,3Z)-butadiene-4-N,N-dimethylamines”, Org. Biomol. Chem., 10:30 (2012), 5795
V. Yu. Rozhkov, L. V. Batog, M. I. Struchkova, “Synthesis of 3-nitramino-4-(1H-1,2,3-triazol-1-yl)-1,2,5-oxadiazoles and their salts”, Russ Chem Bull, 60:8 (2011), 1712
Marco Florian Schmidt, Albert Isidro‐Llobet, Michael Lisurek, Adeeb El‐Dahshan, Jinzhi Tan, Rolf Hilgenfeld, Jörg Rademann, “Sensibilisierte Detektion inhibitorischer Fragmente und iterative Entwicklung nicht‐peptidischer Proteaseinhibitoren durch dynamisches Ligationsscreening”, Angewandte Chemie, 120:17 (2008), 3319
Marco Florian Schmidt, Albert Isidro‐Llobet, Michael Lisurek, Adeeb El‐Dahshan, Jinzhi Tan, Rolf Hilgenfeld, Jörg Rademann, “Sensitized Detection of Inhibitory Fragments and Iterative Development of Non‐Peptidic Protease Inhibitors by Dynamic Ligation Screening”, Angew Chem Int Ed, 47:17 (2008), 3275
G. Nikonov, S. Bobrov, Comprehensive Heterocyclic Chemistry III, 2008, 315
V. Yu. Rozhkov, L. V. Batog, M. I. Struchkova, “Synthesis of 1,2,4-oxadiazole-, pyrrole- and 1,2,3-triazole-substituted (1,2,3-triazol-1-yl)furazans”, Mendeleev Commun., 18:3 (2008), 161–163
V. Yu. Rozhkov, L. V. Batog, M. I. Struchkova, “Nucleophilic substitution in the series of (1,2,3-triazol-1-yl)-1,2,5-oxadiazoles. Reactions with N-, O-, and S-nucleophiles”, Russ Chem Bull, 54:8 (2005), 1923
L. V. Batog, L. S. Konstantinova, V. Yu. Rozhkov, “Synthesis of nitro, nitroso, azo, and azido derivatives of (4-R1-5-R2-1,2,3-triazol-1-yl)-1,2,5-oxadiazoles by oxidation and diazotization of the corresponding amines”, Russ Chem Bull, 54:8 (2005), 1915
V. Yu. Rozhkov, L. V. Batog, E. K. Shevtsova, M. I. Struchkova, “Synthesis and Dimroth rearrangement of 3-amino-4-(5-amino-1H-1,2,3-triazol-1-yl)-1,2,5-oxadiazoles”, Mendeleev Commun., 14:2 (2004), 76–77
Lyudmila V. Batog, Vladimir Yu. Rozhkov, Marina I. Struchkova, “Azido‐1,2,5‐oxadiazoles in Reactions with 1,3‐Dicarbonyl Compounds.”, ChemInform, 34:3 (2003)
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