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Synthesis of Diazanorcaradienes and 1,2‐Diazepines via the Tandem [4+2]‐Cycloaddition/Retro‐[4+2]‐Cycloaddition Reaction between Methoxycarbonylcyclopropenes and Dimethoxycarbonyltetrazine Full article

Journal European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690
Output data Year: 2019, Volume: 2019, Number: 26, Pages: 4133-4138 Pages count : 6 DOI: 10.1002/ejoc.201801861
Authors Belyy Alexander Yu. 1 , Levina Anastasia A. 1 , Platonov Dmitry N. 1 , Salikov Rinat F. 1 , Medvedev Michael G. 2,3,1,4 , Tomilov Yury V. 1
Affiliations
1 N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prospect, 119991 Moscow Russian Federation
2 A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119991 Moscow Russian Federation
3 Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1/3, Moscow, 119991 Russian Federation
4 National Research University Higher School of Economics (HSE), Myasnitskaya str. 20, Moscow, 101000 Russian Federation

Abstract: The reaction of di(methoxycarbonyl)tetrazine with substituted cycloprop-2-ene-1-carboxylates gives a series of 3,4-diazanorcaradienes and 1,2-diazepines. The influence of the nature of cyclopropenes and the reaction conditions on its selectivity was investigated. The addition of nucleophiles to norcaradienes was studied and a rare example of the “walk” rearrangement in this class of compounds was revealed.
Cite: Belyy A.Y. , Levina A.A. , Platonov D.N. , Salikov R.F. , Medvedev M.G. , Tomilov Y.V.
Synthesis of Diazanorcaradienes and 1,2‐Diazepines via the Tandem [4+2]‐Cycloaddition/Retro‐[4+2]‐Cycloaddition Reaction between Methoxycarbonylcyclopropenes and Dimethoxycarbonyltetrazine
European Journal of Organic Chemistry. 2019. V.2019. N26. P.4133-4138. DOI: 10.1002/ejoc.201801861 WOS Scopus OpenAlex
Identifiers:
≡ Web of science: WOS:000475679400006
≡ Scopus: 2-s2.0-85062777738
≡ OpenAlex: W2912933790
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