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Reactions of 2-Nitro-1H-benzo[f]chromenes and 3-Nitro-1-benzofurans with Nucleophiles.
- Source :
-
Russian Journal of Organic Chemistry . Mar2023, Vol. 59 Issue 3, p422-437. 16p. - Publication Year :
- 2023
-
Abstract
- 2-Nitro-1H-benzo[f]chromenes reacted with alcohols to give a series of 3-alkoxy-2-nitro-2,3-dihy-dro-1H-benzo[f]chromenes as mixtures of cis and trans isomers. The reaction of 2-nitro-1H-benzo[f]chromenes with cyclic secondary amines and 3-amino-5,5-dimethylcyclohex-2-en-1-one displayed trans diastereoselec-tivity with the formation of Michael adducts with benzochroman structure. Conjugate addition of substituted anilines to the title chromenes afforded (2-hydroxynaphthalen-1-ylmethyl)-substituted β-nitroenamines. Nucleophilic dearomatization of 3-nitrobenzofurans by the action of primary aromatic amines involved aza- and retro-oxa-Michael reactions, which demonstrated a strong tendency of 3-nitrobenzofurans to undergo opening of the furan ring. [ABSTRACT FROM AUTHOR]
- Subjects :
- *NUCLEOPHILES
*SECONDARY amines
*ISOMERS
*MICHAEL reaction
*ANILINE
*AROMATIC amines
Subjects
Details
- Language :
- English
- ISSN :
- 10704280
- Volume :
- 59
- Issue :
- 3
- Database :
- Academic Search Index
- Journal :
- Russian Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 163726537
- Full Text :
- https://doi.org/10.1134/S1070428023030107