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Concise Route to a Series of Novel 3-(tetrazol-5-yl)quinoxalin-2(1H)-ones

Concise Route to a Series of Novel 3-(tetrazol-5-yl)quinoxalin-2(1H)-ones

Steven Gunawan, Gary Nichol, Christopher Hulme

Tetrahedron Lett. 2012 Mar 28;53(13):1664-1667.

PMID: 22707799

Abstract:

This report 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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AS212495	Benzodiazepine Multi-component Mixture-8 solution			Price

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