Abstract:
The decomposition of N-cyclopropyl-N-nitrosourea with K2CO3 generates a cyclopropyldiazonium intermediate, which is trapped in situ with 1- and 2-naphthols, 2,7-dihydroxynaphthalene or 8-hydroxyquinoline to afford azo coupling products.
Document Type:
Article
Language: English
Citation:
Yu. V. Tomilov, I. V. Kostyuchenko, E. V. Shulishov, O. M. Nefedov, “Formation of cyclopropylazoarenes in the azo coupling reactions of the cyclopropanediazonium ion with active aromatic compounds”, Mendeleev Commun., 12:3 (2002), 104–106
Linking options:
https://www.mathnet.ru/eng/mendc4114
https://www.mathnet.ru/eng/mendc/v12/i3/p104
This publication is cited in the following 12 articles:
Nataliya Zaitseva, Sergei Alekseev, Vladimir Zaitsev, Viktoria Raks, “Solid-Phase Spectrophotometric Analysis of 1-Naphthol Using Silica Functionalized with m-Diazophenylarsonic Acid”, Nanoscale Res Lett, 11:1 (2016)
Luís Duarte, Barbara Michela Giuliano, Igor Reva, Rui Fausto, “Tautomers and UV-Induced Photoisomerization of a Strongly Intramolecularly H-Bonded Aromatic Azo-Dye: 1-(Cyclopropyl)diazo-2-naphthol”, J. Phys. Chem. A, 117:41 (2013), 10671
Yu. V. Tomilov, I. V. Kostyuchenko, A. I. Novichkov, E. V. Shulishov, “Formation of tetrazoles on diazocyclopropane generation”, Mendeleev Commun., 21:6 (2011), 302–304
E. V. Shulishov, I. P. Klimenko, V. A. Korolev, I. V. Kostyuchenko, G. P. Okonnishnikova, Yu. V. Tomilov, “Azo-coupling and reduction of cyclopropanediazonium ions in the reactions with polyhydroxyarenes and aminophenols”, Russ Chem Bull, 57:8 (2008), 1703
R. A. Novikov, I. P. Klimenko, E. V. Shulishov, V. A. Korolev, Yu. V. Tomilov, “Thermal transformation of cyclopropylazoarenes into the five-membered nitrogen-containing heterocycles”, Russ Chem Bull, 57:8 (2008), 1718
Yury V. Tomilov, Dmitry N. Platonov, Rinat F. Salikov, Galina P. Okonnishnikova, “Synthesis and properties of stable 1,2,3,4,5,6,7-heptamethoxycarbonylcyclohepta-2,4,6-trien-1-yl potassium and its reactions with electrophilic reagents”, Tetrahedron, 64:44 (2008), 10201
Yu. V. Tomilov, I. V. Kostyuchenko, G. P. Okonnishnikova, I. P. Klimenko, E. V. Shulishov, “Decomposition of N-cyclopropyl-N-nitrosourea in the presence of reducing agents as a new way of generating the cyclopropyl radical”, Russ Chem Bull, 55:11 (2006), 2008
G. P. Okonnishnikova, I. V. Kostyuchenko, E. V. Shulishov, Yu. V. Tomilov, “Transformations of 5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one under various conditions of cyclopropyldiazonium generation”, Russ Chem Bull, 55:12 (2006), 2233
I. P. Klimenko, V. A. Korolev, Yu. V. Tomilov, O. M. Nefedov, “Generation of cyclopropanediazonium and its chemical transformations in the presence of phenol”, Russ J Org Chem, 42:9 (2006), 1299
Yu. V. Tomilov, D. N. Platonov, D. V. Dorokhov, I. V. Kostyuchenko, “Cascade reactions of nitrogen-and phosphorus-containing ylides with methyl diazoacetate and in situ generated diazocyclopropane”, Russ Chem Bull, 55:1 (2006), 112
Yury V. Tomilov, Ekaterina V. Guseva, Irina V. Kostuchenko, Bogdan I. Ugrak, Evgeny V. Shulishov, Oleg M. Nefedov, “Fluorinated β‐Diketones in Reactions with Diazocyclopropane Generated in situ”, Eur J Org Chem, 2004:14 (2004), 3145
Yury V. Tomilov, Irina V. Kostyuchenko, Evgeny V. Shulishov, Oleg M. Nefedov, “Formation of Cyclopropylazoarenes in the Azo Coupling Reactions of the Cyclopropanediazonium Ion with Active Aromatic Compounds.”, ChemInform, 33:46 (2002), 55
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