Abstract:
New thermally induced rearrangements in the furoxan series have been found: transformation of 3-(R)-substituted 4-(3-ethoxy-carbonylthioureido)-1,2,5-oxadiazole 2-oxides (furoxans) into derivatives of 5-amino-3-(α-nitroalkyl)-1,2,4-thiadiazole for R = Me, Ph, MeCO and into (5-amino-1,2,4-thiadiazol-3-yl)nitroformaldehyde arylhydrazones for R = N=N–Ar.
Document Type:
Article
Language: English
Citation:
S. I. Molotov, A. S. Kulikov, N. N. Makhova, K. A. Lyssenko, “Thermal rearrangements of 3-substituted 4-(3-ethoxycarbonylthioureido)-1,2,5-oxadiazole 2-oxides”, Mendeleev Commun., 13:4 (2003), 188–190
Linking options:
https://www.mathnet.ru/eng/mendc4017
https://www.mathnet.ru/eng/mendc/v13/i4/p188
This publication is cited in the following 11 articles:
Egor S. Zhilin, Leonid L. Fershtat, Dmitry M. Bystrov, Alexander S. Kulikov, Artem O. Dmitrienko, Ivan V. Ananyev, Nina N. Makhova, “Renaissance of 1,2,5‐Oxadiazolyl Diazonium Salts: Synthesis and Reactivity”, Eur J Org Chem, 2019:26 (2019), 4248
Dmitry M. Bystrov, Leonid L. Fershtat, Nina N. Makhova, “Synthesis and reactivity of aminofuroxans”, Chem Heterocycl Comp, 55:12 (2019), 1143
S. I. Molotov, A. S. Kulikov, K. A. Lyssenko, N. N. Makhova, “Base-induced rearrangement of 4-amidino-3-R-furoxans into 1-substituted 3-(1-nitroalkyl)-5-R-1H-1,2,4-triazoles”, Russ Chem Bull, 62:5 (2013), 1238
N. N. Makhova, A. S. Kulikov, “Advances in the chemistry of monocyclic amino- and nitrofuroxans”, Russian Chem. Reviews, 82:11 (2013), 1007–1033
Ugo Chiacchio, Giovanni Romeo, Modern Heterocyclic Chemistry, 2011, 1253
G. Nikonov, S. Bobrov, Comprehensive Heterocyclic Chemistry III, 2008, 315
Ana Castro, Tania Castaño, Arantxa Encinas, Williams Porcal, Carmen Gil, “Advances in the synthesis and recent therapeutic applications of 1,2,4-thiadiazole heterocycles”, Bioorganic & Medicinal Chemistry, 14:5 (2006), 1644
S. I. Molotov, M. A. Epishina, A. S. Kulikov, Yu. V. Nelyubina, K. A. Lyssenko, K. Yu. Suponitsky, N. N. Makhova, “Thermally induced rearrangement of the arylhydrazones of furoxan-3-yl carbonyl compounds”, Mendeleev Commun., 16:5 (2006), 259–262
Paraskevi Supsana, Theodoros Liaskopoulos, Stavroula Skoulika, Antonios Kolocouris, Petros G. Tsoungas, George Varvounis, “Thermal rearrangement of spiro[naphthalene(naphthopyranofurazan)]oxides to spiro[naphthalene(phenalenofurazan)oxides. A probable furazan oxide triggered tandem isomerisation process”, Tetrahedron, 61:25 (2005), 6131
Sergey I. Molotov, Alexander S. Kulikov, Nina N. Makhova, Konstantin A. Lyssenko, “Thermal Rearrangements of 3‐Substituted 4‐(3‐Ethoxycarbonylthioureido)‐1,2,5‐oxadiazole 2‐Oxides.”, ChemInform, 35:3 (2004)
I. V. Ovchinnikov, M. A. Epishina, S. I. Molotov, Yu. A. Strelenko, K. A. Lyssenko, N. N. Makhova, “New rearrangement of azofuroxans in an oxidising medium”, Mendeleev Commun., 13:6 (2003), 272–275
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