Synthesis of 2-aminochromene derivatives from 1-(2-imino-2H-chromen-3-yl)pyridin-1-ium perchlorates and nitromethane in basic medium

[Figure not available: see fulltext.] Novel 2-amino-4-(nitromethylidene)chromenes were obtained as a result of the reaction of 1-(2-imino-2H-chromen-3-yl)pyridinium perchlorates and nitromethane by the action of DBU at reflux in trifluoroethanol. The starting 2-iminochromenes are readily accessible from the corresponding salicylic aldehydes and quaternary cyanomethyl pyridinium salts. The reaction is tolerant to substituents of different nature (alkyl, alkoxy, halogen); a limitation is the presence of strong electron-withdrawing substituents in the benzene ring of chromene. During the reaction, the products precipitate and can be isolated by filtration. © 2020, Springer Science+Business Media, LLC, part of Springer Nature.

Publisher
Латвийский институт органического синтеза Латвийской академии наук / Springer New York Consultants Bureau
Number of issue
9
Language
English
Pages
1161-1166
Status
Published
Volume
56
Year
2020
Organizations
  • 1 RUDN University, 6 Miklukho-Maklaya St., Moscow, 117198, Russian Federation
Keywords
2-aminochromene; 2-iminochromene; Michael addition; nitromethane; β-elimination
Date of creation
20.04.2021
Date of change
20.04.2021
Short link
https://repository.rudn.ru/en/records/article/record/72638/
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