Regioselective Synthesis of Substituted Carbazoles, Bicarbazoles, and Clausine C
Substituted carbazoles are efficiently constructed from 3-triflato-2-pyrones and alkynyl anilines. Multiple substituents are tolerated on the carbazole, and complete control of regiochemistry is observed. Complicated and sterically congested substitution patterns are produced. This strategy is also used to prepare substituted bicarbazoles and related biaryls. Finally, the method was showcased in a synthesis of the carbazole natural product clausine C.
Points, Gary L.,Beaudry, Christopher M.
supporting information
p. 6882 - 6885
(2021/09/11)
[3+2]-Annulation of platinum-bound azomethine ylides with distal C=C bonds of N-allenamides
A Pt-catalyzed, highly regioselective reaction between N-allenamides and imino-alkynes leading to pyrrolo[1,2-a]indoles is described. This represents the first example of [3+2]-annulation of Pt-bound azomethine ylides with the distal C=C bond of N-allenam
A robust, well-defined homogeneous silver(I) catalyst for mild intramolecular hydroamination of 2-ethynylanilines leading to indoles
A highly efficient, chemically stable and well-defined homogeneous silver(I) catalyst is reported for the room temperature, intramolecular hydroamination of 2-alkynylanilines leading to indole derivatives. Copyright
McNulty, James,Keskar, Kunal
p. 1622 - 1629
(2014/03/21)
A Robust, Well-Defined Homogeneous Silver(I) Catalyst for Mild Intramolecular Hydroamination of 2-Ethynylanilines Leading to Indoles
A highly efficient, chemically stable and well-defined homogeneous silver(I) catalyst is reported for the room temperature, intramolecular hydroamination of 2-alkynylanilines leading to indole derivatives.
McNulty, James,Keskar, Kunal
p. 1622 - 1629
(2015/10/05)
InBr3-promoted divergent approach to polysubstituted indoles and quinolines from 2-ethynylanilines: Switch from an intramolecular cyclization to an intermolecular dimerization by a type of terminal substituent group
(Chemical Equation Presented) Use of a 2-ethynylaniline having an alkyl or aryl group on the terminal alkyne selectively produced a variety of polyfunctionalized indole derivatives in moderate to excellent yields via indium-catalyzed intramolecular cyclization of the corresponding alkynylaniline. In contrast, employment of a substrate with a trimethylsilyl group or with no substituent group on the terminal triple bond, exclusively afforded polysubstituted quinoline derivatives in good yields via indium-promoted intermolecular dimerization of the ethynylaniline. This indium catalytic system successfully accommodated the intramolecular cyclization of other arylalkyne skeletons involving a carboxylic acid and an amide group.