Michael addition to 3-(2-nitrovinyl)indoles – route toward aliphatic nitro compounds with heterocyclic substituents

[Figure not available: see fulltext.] Synthetic approach toward indole derivatives bearing 2-nitroethyl group and polar azole moiety has been developed. This method involves conjugate addition of 1,3-dicarbonyl compounds to 3-(2-nitrovinyl)-1H-indoles followed by cyclocondensation with hydrazine or hydroxylamine to furnish pyrazole or isoxazole ring. Application of microwave activation allows to obtain the target indole derivatives in short time and avoid protection of indole nitrogen atom. © 2019, Springer Science+Business Media, LLC, part of Springer Nature.

Authors
Aksenov N.A. 1 , Skomorokhov A.A.1 , Aksenov A.V. 1 , Voskressensky L.G. 2 , Rubin M.A.1, 3
Editors
-
Publisher
Латвийский институт органического синтеза Латвийской академии наук / Springer New York Consultants Bureau
Number of issue
6
Language
English
Pages
541-546
Status
Published
Department
-
Number
-
Volume
55
Year
2019
Organizations
  • 1 North-Caucasus Federal University, 1a Pushkina St., Stavropol, 355009, Russian Federation
  • 2 RUDN University, 6 Miklukho-Maklaya St., Moscow, 117198, Russian Federation
  • 3 The University of Kansas, 1567 Irving Hill Rd, Lawrence, KS 66045-7582, United States
Keywords
indole; isoxazole; Michael addition; microwave-assisted synthesis; nitroalkene; pyrazole
Date of creation
24.12.2019
Date of change
24.12.2019
Short link
https://repository.rudn.ru/en/records/article/record/55193/