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Mendeleev Communications, 2011, Volume 21, Issue 1, Pages 50–52
DOI: https://doi.org/10.1016/j.mencom.2011.01.021
(Mi mendc2864)
 

This article is cited in 16 scientific papers (total in 16 papers)

New approach to N,N-dialkoxy-N′-arylureas and N,N-dialkoxycarbamates

V. G. Shtamburga, A. V. Tsygankovb, M. V. Gerasimenkoa, O. V. Shishkincd, R. I. Zubatyukc, A. V. Mazepae, R. G. Kostyanovskyf

a Ukrainian State University of Chemical Technology, Dnepropetrovsk, Ukraine
b State Flight Academy of Ukraine, Kirovograd, Ukraine
c STC 'Institute for Single Crystals', National Academy of Sciences of Ukraine, Kharkov, Ukraine
d Department of Chemistry, V.N. Karazin Khar'kov National University, Khar'kov, Ukraine
e A.V. Bogatsky Physico-Chemical Institute, National Academy of Sciences of Ukraine, Odessa, Ukraine
f N.N. Semenov Federal Research Center for Chemical Physics, Russian Academy of Sciences, Moscow, Russian Federation
Abstract: Methanolysis of N-chloro-N-alkoxy-N’-arylureas in the presence of silver trifluoroacetate gives the corresponding N,N-dialkoxy-N’-arylureas, whereas N-chloro-N-alkoxycarbamates react with alcohols in the presence of silver trifluoroacetate to afford N,N-dialkoxycarbamates.
Document Type: Article
Language: English
Supplementary materials:
Supplementary_data_1.pdf (111.5 Kb)


Citation: V. G. Shtamburg, A. V. Tsygankov, M. V. Gerasimenko, O. V. Shishkin, R. I. Zubatyuk, A. V. Mazepa, R. G. Kostyanovsky, “New approach to N,N-dialkoxy-N′-arylureas and N,N-dialkoxycarbamates”, Mendeleev Commun., 21:1 (2011), 50–52
Linking options:
  • https://www.mathnet.ru/eng/mendc2864
  • https://www.mathnet.ru/eng/mendc/v21/i1/p50
  • This publication is cited in the following 16 articles:
    1. V.G. Shtamburg, E.A. Klots, V.V. Shtamburg, A.A. Anishchenko, S.V. Shishkina, S.V. Kravchenko, A.V. Mazepa, “Structure of N-acetoxy-N-benzyloxyurea”, Vopr. Khim. Khim. Tekhnol., 2024, no. 4, 88  crossref
    2. Stephen A. Glover, Adam A. Rosser, Amide Bond Activation, 2022, 29  crossref
    3. Stephen A. Glover, Adam A. Rosser, “The role of substituents in the HERON reaction of anomeric amides”, Can. J. Chem., 94:12 (2016), 1169  crossref
    4. Ramón Armenta, Juan I. Sarmiento-Sánchez, “Synthesis of 1,3-dihydro-2H-benzimidazol-2-ones (microreview)”, Chem Heterocycl Comp, 52:12 (2016), 1002  crossref
    5. V. G. Shtamburg, S. V. Shishkina, V. V. Shtamburg, A. V. Mazepa, G. K. Kadorkina, R. G. Kostyanovsky, “1-Alkoxyamino-4-dimethylaminopyridinium salts: synthesis and structure†”, Mendeleev Commun., 26:2 (2016), 169–171  mathnet  crossref
    6. V. G. Shtamburg, R. G. Kostyanovsky, A. V. Tsygankov, V. V. Shtamburg, O. V. Shishkin, R. I. Zubatyuk, A. V. Mazepa, S. V. Kravchenko, “Geminal systems”, Russ Chem Bull, 64:1 (2015), 62  crossref
    7. Xuming Li, Liu Yang, Xiang Zhang, Daisy Zhang-Negrerie, Yunfei Du, Kang Zhao, “Construction of 1,4-Benzodiazepine Skeleton from 2-(Arylamino)benzamides through PhI(OAc)2-Mediated Oxidative C–N Bond Formation”, J. Org. Chem., 79:3 (2014), 955  crossref
    8. V. G. Shtamburg, O. V. Shishkin, V. V. Shtamburg, R. I. Zubatyuk, A. V. Mazepa, R. G. Kostyanovsky, “N-Alkoxy-N-chloroureas in the synthesis of 3,4-dihydro-1H-2,1-benzoxazine-1-carboxamide and 1-alkoxy-1,3-dihydrobenzimidazol-2-ones”, Chem Heterocycl Comp, 49:8 (2013), 1195  crossref
    9. Ningning Zhang, Rui Yang, Daisy Zhang-Negrerie, Yunfei Du, Kang Zhao, “Direct Conversion ofN-Alkoxyamides to Carboxylic Esters through Tandem NBS-Mediated Oxidative Homocoupling and Thermal Denitrogenation”, J. Org. Chem., 78:17 (2013), 8705  crossref
    10. S. Kubik, Knowledge Updates 2013/3, 2013  crossref
    11. V. G. Shtamburg, A. V. Tsygankov, O. V. Shishkin, R. I. Zubatyuk, V. V. Shtamburg, M. V. Gerasimenko, A. V. Mazepa, R. G. Kostyanovsky, “1-Alkoxyamino-4-dimethylaminopyridinium derivatives as new representatives of O–N–N+ geminal systems and their structure†”, Mendeleev Commun., 22:2 (2012), 92–94  mathnet  crossref
    12. V. G. Shtamburg, A. V. Tsygankov, O. V. Shishkin, R. I. Zubatyuk, B. V. Uspensky, V. V. Shtamburg, A. V. Mazepa, R. G. Kostyanovsky, “The properties and structure of N-chloro-N-methoxy-4-nitrobenzamide”, Mendeleev Commun., 22:3 (2012), 164–166  mathnet  crossref
    13. Stephen A. Glover, Jonathan M. White, Adam A. Rosser, Katherine M. Digianantonio, “Structures of N,N-Dialkoxyamides: Pyramidal Anomeric Amides with Low Amidicity”, J. Org. Chem., 76:23 (2011), 9757  crossref
    14. Katherine M. Digianantonio, Stephen A. Glover, Jennifer P. Johns, Adam A. Rosser, “Synthesis and thermal decomposition of N,N-dialkoxyamides”, Org. Biomol. Chem., 9:11 (2011), 4116  crossref
    15. Vasiliy G. Shtamburg, Alexander V. Tsygankov, Mikhail V. Gerasimenko, Oleg V. Shishkin, Roman I. Zubatyuk, Alexander V. Mazepa, Remir G. Kostyanovsky, “ChemInform Abstract: New Approach to N,N‐Dialkoxy‐N′‐arylureas and N,N‐Dialkoxycarbamates.”, ChemInform, 42:26 (2011)  crossref
    16. V. G. Shtamburg, E. A. Klots, M. V. Gerasimenko, O. V. Shishkin, R. I. Zubatyuk, R. G. Kostyanovsky, “N,3-Dimethyl-3-(perhydro-1,3,2-dioxazepin-2-yl)butanamide: synthesis and crystal structure”, Mendeleev Commun., 21:6 (2011), 349–350  mathnet  crossref
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