Direct Conversion of 3-(2-Nitroethyl)-1H-Indoles into 2-(1H-Indol-2-yl)Acetonitriles

The recently discovered [4+1]-spirocyclization of nitroalkenes to indoles provided a convenient new approach to 2-(1H-indol-2-yl)acetonitriles. However, this reaction was complicated by the formation of inert 3-(2-nitroethyl)-1H-indole byproducts. Herein, we offer a workaround this problem that allo...

Full description

Saved in:
Bibliographic Details
Published inMolecules (Basel, Switzerland) Vol. 26; no. 20; p. 6132
Main Authors Aksenov, Alexander V., Aksenov, Nicolai A., Aleksandrova, Elena V., Aksenov, Dmitrii A., Grishin, Igor Yu, Sorokina, Elena A., Wenger, Allison, Rubin, Michael
Format Journal Article
LanguageEnglish
Published Basel MDPI AG 11.10.2021
MDPI
Subjects
1,2-alkyl shift
Acetonitrile
Acids
Byproducts
cascade transformations
Chloride
Chromatography
Direct conversion
heterocycles
Hydrocarbons
Indoles
nitroalkanes
rearrangements
Online AccessGet full text

Cover

More Information
Summary:The recently discovered [4+1]-spirocyclization of nitroalkenes to indoles provided a convenient new approach to 2-(1H-indol-2-yl)acetonitriles. However, this reaction was complicated by the formation of inert 3-(2-nitroethyl)-1H-indole byproducts. Herein, we offer a workaround this problem that allows for effective transformation of the unwanted byproducts into acetonitrile target molecules.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules26206132