Abstract:
Simple and efficient methods have been developed to obtain cyanomethylamines and azidomethylamines using reactions of methoxymethylamines with TMSCN and TMSN3, respectively. In the case of dimethylformamide dimethylacetal, only one MeO group was substituted with CN, and an unexpected direction of the subsequent azidation was found. Adducts of azidomethylamines with DMAD were studied, and the base-catalyzed isomerization of symmetric triazoles into non-symmetric ones was revealed.
Document Type:
Article
Language: English
Citation:
O. G. Nabiev, Z. O. Nabizade, R. G. Kostyanovsky, “Cyanomethylamines and azidomethylamines: new general methods of the synthesis and transformations”, Mendeleev Commun., 19:5 (2009), 281–283
Linking options:
https://www.mathnet.ru/eng/mendc3200
https://www.mathnet.ru/eng/mendc/v19/i5/p281
This publication is cited in the following 10 articles:
Klaus Banert, Tom Pester, “Too Short-Lived or Not Existing Species: N-Azidoamines Reinvestigated”, J. Org. Chem., 84:7 (2019), 4033
Parham Taslimi, Cuneyt Caglayan, Vagif Farzaliyev, Oruj Nabiyev, Afsun Sujayev, Fikret Turkan, Ruya Kaya, İlhami Gulçin, “Synthesis and discovery of potent carbonic anhydrase, acetylcholinesterase, butyrylcholinesterase, and α‐glycosidase enzymes inhibitors: The novel N,N′‐bis‐cyanomethylamine and alkoxymethylamine derivatives”, J Biochem & Molecular Tox, 32:4 (2018)
Paulina E. Gonzalez, Hemant K. Sharma, Sanchita Chakrabarty, Alejandro Metta‐Magaña, Keith H. Pannell, “Triethylsiloxymethyl‐N,N‐dimethylamine, Et3SiOCH2NMe2: A Dimethylaminomethylation (Mannich) Reagent for O–H, S–H, P–H and Aromatic C–H Systems”, Eur J Org Chem, 2017:37 (2017), 5610
Klaus Banert, Patai's Chemistry of Functional Groups, 2017, 1
E. P. Al'tova, R. G. Kostyanovskii, I. F. Shishkov, “Molecular structure of (cyanomethoxy)(dimethylamino)methane as studied by gas-phase electron diffraction and quantum-chemical calculations”, Russ. J. Phys. Chem., 88:4 (2014), 667
R. G. Kostyanovsky, K. A. Lyssenko, O. G. Nabiev, G. K. Kadorkina, I. I. Chervin, “Novel 1,10-diaza-18-crown-6 derivatives”, Russ Chem Bull, 63:3 (2014), 772
Nataliya Belskaya, Julia Subbotina, Svetlana Lesogorova, Topics in Heterocyclic Chemistry, 40, Chemistry of 1,2,3-triazoles, 2014, 51
E. P. Altova, O. G. Nabiev, N. M. Karasev, R. G. Kostyanovsky, L. S. Khaikin, I. F. Shishkov, “Molecular Structure of N-azidomethyl-N,N-dimethylamine According to Gas-phase Electron Diffraction Data and Quantum-chemical Calculations”, Mendeleev Commun., 23:3 (2013), 166–167
Olga V. Dorofeeva, Alexander V. Mitin, Ekaterina P. Altova, Nikolai M. Karasev, Orudzh G. Nabiev, Lev V. Vilkov, Heinz Oberhammer, “Anomeric effect in N-azidomethylpyrrolidine: gas-phase electron diffraction and theoretical study”, Phys. Chem. Chem. Phys., 13:4 (2011), 1490
Orudzh G. Nabiev, Zargalam O. Nabizade, Remir G. Kostyanovsky, “ChemInform Abstract: Geminal Systems. Part 58. Cyanomethylamines and Azidomethylamines: New General Methods of the Synthesis and Transformations.”, ChemInform, 41:6 (2010)