The Niementowski quinazoline synthesis is the chemical reaction of anthranilic acids with amides to form 4-oxo-3,4-dihydroquinazolines (3H-quinazolin-4-ones).[1][2][3]
| Niementowski quinazoline synthesis | |
|---|---|
| Named after | Stefan Niementowski |
| Reaction type | Ring forming reaction |
Uses
editResearch has demonstrated that the Niementowski quinazoline synthesis could be employed for the creation of potential EGFR-inhibiting molecules. Hensbergen et al.[4] 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
edit- ^ Von Niementowski, Stefan (1895). "Synthesen von Chinazolinverbindungen". J. Prakt. Chem. (in German). 51 (1): 564–572. doi:10.1002/prac.18950510150.
- ^ 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.
- ^ 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.
- ^ 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.