Аннотация:N-Alkoxy-N-(1-pyridinium)urea salts 3, 4 have been prepared, the conversions of N-acetoxy-N-methoxyurea 7 into N,N-dimethoxyurea 8 and of N-n-propyloxy-N-(1-pyridinium)-N',N'-dimethylurea chloride 6 into N,N-dimethoxy-N',N'-dimethylurea 11 were carried out. A high pyramidality of the amide nitrogen in O–N–X groups [X = N+C5H5, OMe, OC(O)C6H4Cl-p] has been revealed by XRD studies of ureas 3b, 8 and N-p-chlorobenzoyloxy-N-n-butyloxyurea 9.
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V. G. Shtamburg, O. V. Shishkin, R. I. Zubatyuk, S. V. Kravchenko, A. V. Tsygankov, V. V. Shtamburg, V. B. Distanov, R. G. Kostyanovsky, “Synthesis, structure and properties of N-alkoxy-N-(1-pyridinium)urea salts, N-alkoxy-N-acyloxyureas and N,N-dialkoxyureas”, Mendeleev Commun., 17:3 (2007), 178–180
Vasiliy G. Shtamburg, Evgeniy A. Klots, Victor V. Shtamburg, Andrey A. Anishchenko, Svitlana V. Shishkina, Alexander V. Mazepa, “Nucleophilic substitution at nitrogen atom. N-Alkoxy-N-(dimethoxyphosphoryl)ureas, synthesis and structure”, Journal of Molecular Structure, 1277 (2023), 134865
Stephen A. Glover, Adam A. Rosser, Amide Bond Activation, 2022, 29
Stephen A. Glover, Rhiannon R. Schumacher, “Mutagenicity of N-acyloxy-N-alkoxyamides as an indicator of DNA intercalation: The role of fluorene and fluorenone substituents as DNA intercalators”, Mutation Research/Genetic Toxicology and Environmental Mutagenesis, 863-864 (2021), 503299
Stephen A. Glover, Adam A. Rosser, “Heteroatom Substitution at Amide Nitrogen—Resonance Reduction and HERON Reactions of Anomeric Amides”, Molecules, 23:11 (2018), 2834
Stephen A. Glover, Adam A. Rosser, “The role of substituents in the HERON reaction of anomeric amides”, Can. J. Chem., 94:12 (2016), 1169
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
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
Stephen A. Glover, Adam A. Rosser, “HERON reactions of anomeric amides: understanding the driving force”, J of Physical Organic Chem, 28:3 (2015), 215
Stephen A. Glover, Adam A. Rosser, Avat (Arman) Taherpour, Ben W. Greatrex, “Formation and HERON Reactivity of Cyclic N,N-Dialkoxyamides”, Aust. J. Chem., 67:3 (2014), 507
Stephen A. Glover, Adam A. Rosser, Robert M. Spence, “Studies of the Structure, Amidicity, and Reactivity of N-Chlorohydroxamic Esters and N-Chloro-β,β-dialkylhydrazides: Anomeric Amides with Low Resonance Energies”, Aust. J. Chem., 67:9 (2014), 1344
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
V. G. Shtamburg, O. V. Shishkin, R. I. Zubatyuk, V. V. Shtamburg, A. V. Tsygankov, A. V. Mazepa, G. K. Kadorkina, R. G. Kostyanovsky, “Synthesis and structure of N-alkoxyhydrazines and N-alkoxy-N',N',N'-trialkylhydrazinium salts”, Mendeleev Commun., 23:5 (2013), 289–291
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
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
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
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
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
Stephen A. Glover, Patai's Chemistry of Functional Groups, 2010
R. G. Kostyanovsky, V. G. Shtamburg, O. V. Shishkin, R. I. Zubatyuk, V. V. Shtamburg, A. A. Anishchenko, A. V. Mazepa, “Pyramidal nitrogen in the crystal of N-[(benzoyl)-(hydroxy)methyl]-N-benzyloxy-N'-(2-bromophenyl)urea”, Mendeleev Commun., 20:3 (2010), 167–169