Niementowski quinazoline synthesis explained

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

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.

References

1. Von Niementowski. Stefan. Stefan Niementowski. J. Prakt. Chem.. 1895. 51. 1. 564–572. Synthesen von Chinazolinverbindungen. German. 10.1002/prac.18950510150.
2. Book: Williamson, T. A.. Heterocyclic Compounds. 1957. 6. 324–376. The chemistry of quinazoline. R. C.. Elderfield. John Wiley & Sons. New York.
3. Tetrahedron Lett.. 1980. 21. 32. 3029–3032. Benzologs of allopurinol: Synthesis of pyrazolo [4,3-g] and [3,4-f] quinazolinones. Cuny. Eckehard. Lichtenthaler. F. W.. Moser. Alfred. 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. Tetrahedron Lett.. 56. 46. 6478–6483. 10.1016/j.tetlet.2015.10.008.