Niementowski quinazoline synthesis

The Niementowski quinazoline synthesis is the chemical reaction of anthranilic acids with amides to form 4-oxo-3,4-dihydroquinazolines (3H-quinazolin-4-ones).

The Niementowski quinazoline synthesis
Niementowski quinazoline synthesis
Named after Stefan Niementowski
Reaction type Ring forming reaction

Uses

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

A nucleophilic aromatic substitution is combined with the Niementowski reaction and a BOP-mediated ring closure to afford several analogues.

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References
    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. 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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