One-Pot Synthesis of Nuevamine Aza-Analogues by Combined Use of an Oxidative Ugi Type Reaction and Aza-Diels–Alder Cycloaddition

Autor:	Alejandro Islas-Jácome, Eduardo González-Zamora, Atilano Gutierrez‐Carrillo, Miguel A. Garcia-Garibay
Rok vydání:	2013
Předmět:	Molecular complexity Chemistry Atom economy Organic Chemistry Combined use One-pot synthesis Diels alder Amine gas treating Oxidative phosphorylation Combinatorial chemistry Cycloaddition
Zdroj:	Synlett. 25:403-406
ISSN:	1437-2096 0936-5214
DOI:	10.1055/s-0033-1340218
Popis:	A rapid and efficient one-pot synthesis of a series of four novel nuevamine aza-analogues is described based on the oxidative Ugi-type reaction and aza-Diels–Alder reaction as post-functionalization. A simple IBX-mediated oxidation of a secondary amine followed by isonitrile α-addition and finally an aza-Diels–Alder cycloaddition provides the desired compounds in excellent overall yields considering the short reaction time, atom economy, and the molecular complexity of the final products. This protocol presents a highly attractive procedure for the rapid generation of fused polyheterocycles.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::c4d7a5a4461946cb8d5784f4adbfe5cf https://doi.org/10.1055/s-0033-1340218 Zobrazit plný text záznamu