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Niementowski quinazoline synthesis

From Wikipedia, the free encyclopedia
Niementowski quinazoline synthesis
Named afterStefan Niementowski
Reaction typeRing forming reaction

TheNiementowski quinazoline synthesis is thechemical reaction ofanthranilic acids withamides to form 4-oxo-3,4-dihydroquinazolines (3H-quinazolin-4-ones).[1][2][3]

The Niementowski quinazoline synthesis
The Niementowski quinazoline synthesis

Uses

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Research has demonstrated that the Niementowski quinazoline synthesis could be employed for the creation of potentialEGFR-inhibiting molecules. Hensbergenet al.[4] have shown a synthetic route to a new class of privileged tri- and tetra-cyclic quinazolines containing a medium-sized ring.

Anucleophilic aromatic substitution is combined with the Niementowski reaction and aBOP-mediated ring closure to afford several analogues.

References

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  1. ^Von Niementowski, Stefan (1895)."Synthesen von Chinazolinverbindungen".J. Prakt. Chem. (in German).51 (1):564–572.doi:10.1002/prac.18950510150.
  2. ^Williamson, T. A. (1957). "The chemistry of quinazoline". In Elderfield, R. C. (ed.).Heterocyclic Compounds. Vol. 6. New York:John Wiley & Sons. pp. 324–376.
  3. ^Cuny, Eckehard; Lichtenthaler, F. W.; Moser, Alfred (1980). "Benzologs of allopurinol: Synthesis of pyrazolo [4,3-g] and [3,4-f] quinazolinones".Tetrahedron Lett.21 (32):3029–3032.doi:10.1016/S0040-4039(00)77398-9.
  4. ^Hensbergen, Albertus Wijnand; Mills, Vanessa R.; Collins, Ian; Jones, Alan M. (2015)."An expedient synthesis of oxazepino and oxazocino quinazolines"(PDF).Tetrahedron Lett.56 (46):6478–6483.doi:10.1016/j.tetlet.2015.10.008.
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