This Letter presents a novel three step solution phase protocol to synthesize 3-(tetrazol-5-yl)quinoxalin-2(1H)-ones. The strategy utilizes ethyl glyoxalate and mono-N-Boc-protected-o-phenylenediamine derivatives in the Ugi-Azide multi-component reaction (MCR) to generate a unique 1,5-disubstituted tetrazole. Subsequent acid treatment stimulates a simultaneous Boc deprotection and intramolecular cyclization leading to bis-3,4-dihydroquinoxalinone tetrazoles. Direct oxidation using a stable solid-phase radical catalyst (2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO) with ceric ammonium nitrate (CAN) in catalytic fashion initiating aerobic oxidation, completes the entire procedure to generate a series of original unique bis-quinoxalinone tetrazoles. The method was also expanded to produce a bis-benzodiazepine tetrazole.
|Original language||English (US)|
|Number of pages||4|
|State||Published - Mar 28 2012|
- Multi-component reaction
ASJC Scopus subject areas
- Drug Discovery
- Organic Chemistry
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CCDC 932013: Experimental Crystal Structure Determination
Gunawan, S. (Creator), Nichol, G. (Creator) & Hulme, C. (Creator), Cambridge Crystallographic Data Centre, 2013
DOI: 10.5517/cc108ty1, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc108ty1&sid=DataCite