Download PDF
Synthesis 1990; 1990(3): 224-233
DOI: 10.1055/s-1990-26839
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Reactions of 2-(Dialkylamino)arylacetonitriles with Acetylenes Under Basic Conditions. A Simple Synthesis of Substituted Mono and Diketones

T. Zdrojewski* , A. Jończyk
  • *Department of Chemistry, Technical University (Politechnika) Koszykowa 75, PL-00-662 Warsaw, Poland
Further Information

Publication History

Publication Date:
17 September 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

2-(Dialkylamino)arylacetonitriles 1 react with acetylenes 2a,b in dimethyl sulfoxide, powdered sodium hydroxide and triethylbenzylammonium chloride as a catalyst to give 3 and/or 4. The latter are formed via addition of anion 8 to immonium salt 9. The type of product formed depends on the basicity of amino moiety in 3. Furthermore, compound 1 adds to C-1 of acetylene 2c affording the vinyl derivatives 15. The products 3, 4, 11 and 15 are hydrolyzed to give ketones 5-7, 12 and 16, respectively.

      >