UNEXPECTED FORMATION OF 2-ACETYL-3-ARYL-2-METHYL-2,3-DIHYDROQUINAZOLIN-4(1<i>H</i>)-ONES IN THE REACTION OF 2-AMINO-<i>N</i>'-ARYLBENZAMIDINES WITH BUTANEDIONE

Authors

  • W. Szczepankiewicz Silesian University of Technology
  • N. Kuźnik Silesian University of Technology
  • S. Boncel Silesian University of Technology
  • A. Siewniak Silesian University of Technology

DOI:

https://doi.org/10.1007/1693

Keywords:

amidines, butanedione, quinazolines, quinazolinones, cyclization

Abstract

Reactions of 2-amino-N'-arylbenzamidines with butanedione resulted in a formation of 2-acetyl-3-aryl-2-methyl-2,3-dihydroquinazolin-4(1H)-ones, instead of the expected 2-acetyl-4-arylamino-2-methyl-1,2-dihydroquinazolines. The intermediate 1-(3-aryl-4-imino-2-methyl-1,2,3,4-tetrahydroquinazolin-2-yl)ethanones were hydrolyzed to the final products by water molecules present in the reaction medium.

How to Cite
Szczepankiewicz, W.; Kuźnik, N.; Boncel, S.; Siewniak, A. Chem. Heterocycl. Compd. 2014, 50, 1291. [Khim. Geterotsikl. Soedin. 2014, 1400.]

For this article in the English edition see DOI 10.1007/s10593-014-1591-3

Author Biography

W. Szczepankiewicz, Silesian University of Technology

Wojciech Szczepankiewicz.

Department of Organic Chemistry, Bioorganic Chemistry and Biotechnology

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Published

2014-09-25

Issue

No. 9 (2014)

Section

Original Papers