Abstract
The interaction of 4-oxo-3,4-dihydroquinazolinyl- and benzimidazolylacetonitriles with 2,6-dihalobenzaldehydes leads to 3-(2,6-dihalophenyl)-2-(4-oxo-3,4-dihydro-2-quinazolinyl)acrylonitriles and 2-(1H-benzo[d]imidazol-2-yl)-3-(2,6-dihalophenyl)acrylonitriles respectively. As a result of intramolecular cyclization of these nitriles 4-halo-12-oxo-12H-quino[2,1-b]quinazoline-6-carbonitriles and 4-halobenzo[4,5]imidazo[1,2-a]quinoline-6-carbonitriles respectively are formed.
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REFERENCES
I. K. Kacker and S. H. Zaheer, J. Indian Chem. Soc., 28, 344 (1951).
S. Kobayashi, M. Veno, R. Suzuki, H. Ishitani, H.-S. Kim, and Y. Nataya, J. Org. Chem., 64, 6833 (1999).
M. Ishizaki and S. Osada, Jpn. Pat. 06128213; Chem. Abstr., 121, 205215 (1994).
M. Ishizaki and S. Osada, Jpn. Pat. 05339224; Chem. Abstr., 122, 31556 (1995).
M. Ishizaki, S. Nagata, and T. Kobutani, Eur. Patent 506373; Chem. Abstr., 119, 225824 (1993).
J. Fleischer, K. Takacs, and I. Hermecz, J. Heterocycl. Chem., 34, 1251 (1997).
Yu. M. Volovenko, O. V. Khilya, T. A. Volovnenko, and T. V. Shokol, Khim. Geterotsikl. Soedin., 350 (2002).
J. B. Jiang, D. P. Hesson, B. A. Dusak, D. L. Dexter, G. J. Kang, and E. Hamel, J. Med. Chem., 33, 1721 (1990).
Yu. M. Volovenko, O. V. Khilya, and T. A. Volovnenko, in: New Technologies for Obtaining and Applying Biologically Active Substances. Abstracts. International Practical Science Conference, KNTs, Alushta, Krym, Simferopol (2002), p. 15.
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Khilya, O.V., Volovnenko, T.A., Turov, A.V. et al. 4-Oxo-3,4-dihydroquinazolinyl- and Benzimidazolylacetonitriles in Annelation Reactions of a Haloquinoline Ring. Chemistry of Heterocyclic Compounds 40, 1063–1069 (2004). https://doi.org/10.1023/B:COHC.0000046698.75658.49
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DOI: https://doi.org/10.1023/B:COHC.0000046698.75658.49
- benzimidazolylacetonitrile
- 2-(1H-benzo[d]imidazol-2-yl)-3-(2,6-dihalophenyl)acrylonitriles
- 4-halobenzo[4,5]imidazo[1,2-a]quinoline-6-carbonitriles
- 4-halo-12-oxo-12H-quino[2,1-b]-quinazoline-6-carbonitriles
- 3-(2,6-dihalophenyl)-2-(4-oxo-3,4-dihydro-2-quinazolinyl)acrylonitriles
- 4-oxo-3,4-dihydroquinazolinylacetonitrile