Niementowski quinazoline synthesis
{{Reactionbox
| Name = Niementowski quinazoline synthesis
| Type = Ring forming reaction
| NamedAfter = Stefan Niementowski
}}
The Niementowski quinazoline synthesis is the chemical reaction of anthranilic acids with amides to form 4-oxo-3,4-dihydroquinazolines (3H-quinazolin-4-ones).{{Ref|Niementowski1895}}{{Ref|Williamson1957}}{{Ref|Cuny1980}}
Uses
Research has demonstrated that the Niementowski quinazoline synthesis could be employed for the creation of potential EGFR-inhibiting molecules. Hensbergen et al.{{Ref|Hensbergen2015}} have shown a synthetic route to a new class of privileged tri- and tetra-cyclic quinazolines containing a medium-sized ring.
File:Synthesis of oxazepino and oxazocino quinazolines.jpg
A nucleophilic aromatic substitution is combined with the Niementowski reaction and a BOP-mediated ring closure to afford several analogues.
References
{{reflist}}
- {{Note|Niementowski1895}} {{cite journal|last=Von Niementowski|first=Stefan|authorlink=Stefan Niementowski|journal=J. Prakt. Chem.|year=1895|volume=51|issue=1|pages=564–572|title=Synthesen von Chinazolinverbindungen|language=German|doi=10.1002/prac.18950510150|url=https://zenodo.org/record/1427984}}
- {{Note|Williamson1957}} {{cite book|last=Williamson|first=T. A.|title=Heterocyclic Compounds|year=1957|volume=6|pages=324–376|chapter=The chemistry of quinazoline|editor-first=R. C.|editor-last=Elderfield|publisher=John Wiley & Sons|location=New York}}
- {{Note|Cuny1980}} {{cite journal|journal=Tetrahedron Lett.|year=1980|volume=21|issue=32|pages=3029–3032|title=Benzologs of allopurinol: Synthesis of pyrazolo [4,3-g] and [3,4-f] quinazolinones|last1=Cuny|first1=Eckehard|last2=Lichtenthaler|first2=F. W.|last3=Moser|first3=Alfred|doi=10.1016/S0040-4039(00)77398-9}}
- {{Note|Hensberg2015}} {{cite journal|last1 = Hensbergen|first1 = Albertus Wijnand|last2 = Mills|first2 = Vanessa R.|last3 = Collins|first3 = Ian|last4 = Jones|first4 = Alan M.|year = 2015|title = An expedient synthesis of oxazepino and oxazocino quinazolines|journal = Tetrahedron Lett.|volume = 56|issue = 46|pages = 6478–6483|doi = 10.1016/j.tetlet.2015.10.008|url = https://e-space.mmu.ac.uk/579725/1/TettLett%20Paper%20with%20last%20round%20of%20corrections.pdf}}
Category:Condensation reactions
Category:Nitrogen heterocycle forming reactions