4720-37-0Relevant academic research and scientific papers
Rediscovering aminal chemistry: Copper(ii) catalysed formation under mild conditions
Afonso, Carlos A. M.,António, Jo?o P. M.,Gomes, Rafael F. A.,Mendon?a, Ricardo,Pereira, Juliana G.
supporting information, p. 7484 - 7490 (2020/11/18)
Aminals, the N,N analogues of acetals, have been thoroughly explored in organic chemistry, with a particular focus on heteroaromatic aldehyde lithiation. Nevertheless, the existing methodologies for their formation typically employ harsh conditions limiting their usefulness. In this work, we present an efficient and mild methodology for the preparation of aminals from aromatic aldehydes, including furanic platforms. These mild conditions allowed ease of access to a plethora of aminals and as such we set out to explore previously unaccessible potential applications. By studying the stability of various aminals, we were able to develop a simple aldehyde protecting group based on a commercial diamine which is deprotected under mind conditions. We developed a protocol for the scavenging of genotoxic aldehydes by taking advantage of our methodology and a diamine resin, as well as early studies on the development of a stimuli-responsive release system using a salycil aldehyde derived aminal. This journal is
Cyclization of nitroacetamide derivatives with a tethered phenyl ring in triflic acid
Fanté, Bamba,Soro, Yaya,Siaka, Sorho,Marrot, Jér?me,Coustard, Jean-Marie
, p. 969 - 974 (2014/05/06)
N-(3-Hydroxypropyl)-2-nitro-N-(ω-phenylalkyl)acetami-des underwent intramolecular cyclization in triflic acid to afford the corresponding hydroxyimino six- to nine-membered benzofused lactams. The six-membered derivative slowly transformed into 2-(3-hydroxypropyl)isoquinolin-3-one. NMR spectroscopic analysis in situ provided information on the cationic species involved in the reaction, permitting a mechanism to be postulated. This reaction provides a novel and simple route to benzofused lactams.
