Cesium Carbonate-Promoted Hydroamidation of Alkynes: Enamides, Indoles and the Effect of Iron(III) Chloride

A series of enamide derivatives was prepared by a simple procedure for the hydroamidation of alkynes with amides and sulfonamides. The use of such a mild base as cesium carbonate promotes the latter transformation, and the addition of catalytic amounts of iron(III) chloride has a beneficial effect i...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2012-11, Vol.354 (16), p.3054-3064
Main Authors: Herrero, María Teresa, de Sarralde, Jokin Díaz, SanMartin, Raul, Bravo, Laura, Domínguez, Esther
Format: Article
Language:English
Subjects:
Alkynes
Carbonates
Catalysis
Cesium
Chemistry
Chlorides
Derivatives
enamides
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
hydroamidation
Indoles
iron
Noncondensed benzenic compounds
Organic chemistry
Preparations and properties
Transformations
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Summary:A series of enamide derivatives was prepared by a simple procedure for the hydroamidation of alkynes with amides and sulfonamides. The use of such a mild base as cesium carbonate promotes the latter transformation, and the addition of catalytic amounts of iron(III) chloride has a beneficial effect in the outcome of some of the presented hydroamidation reactions. A range of indoles was also synthesized from ortho‐alkynylanilides by both complementary procedures, which proved to be useful for the construction of the indolo[1,2‐c]quinazoline tetracyclic system from an ortho‐(2‐aminophenylalkynyl)anilide.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201200430