Copper(i) catalyzed oxidative hydrolysis of Ugi 3-component and Ugi-azide reaction products towards 2° α-ketoamides and α-ketotetrazoles.

Autor:	Collet JW; Department of Pharmacology and Toxicology, The University of Arizona, 1041 E. Lowell St., Tucson, AZ 85721, USA. hulme@pharmacy.arizona.edu and Department of Chemistry and Pharmaceutical Sciences, VU University Amsterdam, De Boelelaan 1108, 1081HZ, Amsterdam, The Netherlands., Foley C; Department of Pharmacology and Toxicology, The University of Arizona, 1041 E. Lowell St., Tucson, AZ 85721, USA. hulme@pharmacy.arizona.edu., Shaw AY; Department of Pharmacology and Toxicology, The University of Arizona, 1041 E. Lowell St., Tucson, AZ 85721, USA. hulme@pharmacy.arizona.edu., Orru RVA; Department of Chemistry and Pharmaceutical Sciences, VU University Amsterdam, De Boelelaan 1108, 1081HZ, Amsterdam, The Netherlands., Ruijter E; Department of Chemistry and Pharmaceutical Sciences, VU University Amsterdam, De Boelelaan 1108, 1081HZ, Amsterdam, The Netherlands., Hulme C; Department of Pharmacology and Toxicology, The University of Arizona, 1041 E. Lowell St., Tucson, AZ 85721, USA. hulme@pharmacy.arizona.edu.
Jazyk:	angličtina
Zdroj:	Organic & biomolecular chemistry [Org Biomol Chem] 2017 Jul 26; Vol. 15 (29), pp. 6132-6135.
DOI:	10.1039/c7ob00881c
Abstrakt:	Herein, a two-step MCR-oxidation methodology accessing decorated 2° α-ketoamides and α-ketotetrazoles is described via a catalytic copper(i)-mediated C-N oxidation/acidic hydrolysis of Ugi-three-component and Ugi-azide reaction products. The ability to install diversity from aldehyde and isocyanide synthons allows rapid complexity generation. Of note, (1) 2° α-ketoamides are traditionally difficult to access and more so reminiscent of the endogenous peptide bonds. (2) The route to α-keto-tetrazoles is significantly shorter than that in previous reports.
Databáze:	MEDLINE
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