Tandem dinucleophilic cyclization of cyclohexane-1,3-diones with pyridinium salts

Kiamehr, M ; Sharif University of Technology | 2013

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  1. Type of Document: Article
  2. DOI: 10.3762/bjoc.9.124
  3. Publisher: 2013
  4. Abstract:
  5. The cyclization of cyclohexane-1,3-diones with various substituted pyridinium salts afforded functionalized 8-oxa-10-aza-tricyclo[ 2,7]trideca-2(7),11-dienes. The reaction proceeds by regioselective attack of the central carbon atom of the 1,3-dicar-bonyl unit to 4-position of the pyridinium salt and subsequent cyclization by base-assisted proton migration and nucleophilic addition of the oxygen atom to the 2-position, as was elucidated by DFT computations. Fairly extensive screening of bases and additives revealed that the presence of potassium cations is essential for formation of the product
  6. Keywords:
  7. Cyclization ; Density functional calculations ; Heterocycles ; Nucleophilic addition ; Pyridinium salt
  8. Source: Beilstein Journal of Organic Chemistry ; Volume 9 , 2013 , Pages 1119-1126 ; 18605397 (ISSN)
  9. URL: http://www.beilstein-journals.org/bjoc/single/articleFullText.htm?publicId=1860-5397-9-124