Construction of 6-Aminopyridazine Derivatives by the Reaction of Malononitrile with Dichloro-Substituted Diazadienes

The reactions of 4,4-dichloro-1,2-diazabuta-1,3-dienes with malononitrile resulted in an efficient approach to highly functionalized 6-aminopyridazine derivatives isolated in up to 98 %. The process was found to provide straightforward access to the interesting type of nitrogen-containing heterocycles with an exocyclic double bond. Furthermore, the possibility of subsequent functionalization of the obtained compounds via intramolecular cyclization was demonstrated. As a result, condensed azaheterocycles can be prepared very efficiently in one-pot and tandem versions. Finally, the influence of structural features of all synthesized compounds on their absorption characteristics in the UV/Vis-range is also investigated. © 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Authors
Sergeev P.G.1 , Khrustalev V.N. 2, 3 , Nenajdenko V.G. 1
Journal
European Journal of Organic Chemistry
Number of issue
31
Language
English
Pages
4964-4971
Status
Published
Link
External link
DOI
10.1002/ejoc.202000807
Volume
2020
Year
2020
Organizations
  • 1 Department of Chemistry, Lomonosov Moscow State University, Moscow, 119899, Russian Federation
  • 2 Peoples' Friendship University of Russia, Moscow, 117198, Russian Federation
  • 3 N. D. Zelinsky Institute of Organic Chemistry of RAS, 47 Leninsky Prospect, Moscow, 119991, Russian Federation
Keywords
Heterodienes; Nitrogen heterocycles; Nucleophilic substitution; Photophysical properties; Pyridazines
Date of creation
02.11.2020
Date of change
02.11.2020
Short link
https://repository.rudn.ru/en/records/article/record/64472/
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