2-Alkynyl Indole-3-carbonitriles: Synthon for the Regioselective Synthesis of Functionalized 4-Aminocarbazoles
Debanik Panda1, Shivam A Meena1, Manvi Sharma1
1Department of Chemistry, University of Delhi, Delhi 110007, India.
Abstract:
An operationally easy and atom-economical approach for the regioselective tandem synthesis of functionalized 4-aminocarbazoles from easily accessible 2-alkynyl indole-3-carbonitriles under mild reaction conditions has been developed. The developed chemistry involves aza-Henry and successive regioselective annulation to afford the functionalized carbazoles. Replacement of nitromethane with acetophenone led to the formation of the corresponding amino(phenyl)methanone-substituted carbazoles, further extending the diversity of the developed chemistry. The developed methodology accommodates wide functional group variation on the alkyne and is successfully applied for late-stage modification of bioactive molecules.
More Related Videos
Related Concept Videos
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Regioselective Formation of Enolates
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...


