A survey of redox aminations of indoline with aliphatic ketones using bismuth nitrate as catalyst is described. A reaction of an equivalent amount of indoline and aliphatic cyclic and acyclic ketones provides a mixture of excessive alkylated indole derivatives over typically redox isomerization and reductive alkylation pathways while using of the five equivalent of indoline provides N-alkylated indolines as a reductive alkylation product. The desired N-alkyl indoles from the oxidation of N-alkyl indolines were obtained in excellent yields.
in Wiley Online Library (wileyonlinelibrary.com).Bi(NO 3 ) 3 ·5H 2 O-Catalyzed redox amination scope and mechanistic insights of benzylic ketones with indoline are discussed. The experimental results demonstrate that the formation of N-alkyl-substituted indole/indoline derivatives over typically competitive redox and reductive amination processes is depending upon the reaction condition for the benzylic ketones. Scheme 3. Proposed mechanism for the formation 6a and 10a. Scheme 4. Reactions of indoline (1, 1 equiv) with 1-indanone (5e) (1 equiv).Scheme 5. Isomerization attempts of 16. [Color figure can be viewed in the online issue, which is available at wileyonlinelibrary.com.]
An efficient method has been developed for the synthesis of new aza-substituted indoles. The methodology involves a twostep synthesis. The first step involves the Michael addition of indoline with various Michael acceptors. The other includes the oxidation of the indoline ring in the Michael adducts to an indole
The bismuth nitrate-promoted disproportionative condensation of indoles with cyclohexanone in one pot, to yield C3-cyclohexyl substituted indoles and 1,3-di(1H-indol-3-yl)benzene derivatives is reported for the first time.
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