Reductive deprotection of allyl, benzyl and sulfonyl substituted alcohols, amines and amides using a naphthalene-catalysed lithiation

Alonso, Emma; Ramón, Diego J.; Yus, Miguel

doi:10.1016/s0040-4020(97)00920-4

Cited by 129 publications

(48 citation statements)

References 53 publications

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“…Spectral data for N-methylbutyramide (2a) [32], N-methylpivalamide (2b) [32,33], N-methylbenzamide (2c) [34], butyramide (2d) [35], N-phenylbutyramide (2e) [36], N-methyl-3-phenylpropanamide (2f) [37] and N-methylcinnamamide (4b) [38] were consistent with those reported previously. …”

Section: General Procedures For Ruthenium-catalyzed Reduction Of N-alksupporting

confidence: 88%

Ruthenium-catalyzed reduction of N-alkoxy- and N-hydroxyamides

Fukuzawa

Ura

Kataoka

2011

Journal of Organometallic Chemistry

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Section: General Procedures For Ruthenium-catalyzed Reduction Of N-alksupporting

confidence: 88%

Ruthenium-catalyzed reduction of N-alkoxy- and N-hydroxyamides

Fukuzawa

Ura

Kataoka

2011

Journal of Organometallic Chemistry

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“…The reaction proceeded with quantitative yield. 13 1 H NMR (400 MHz, CDCl 3 ): δ[ppm] = 1.519 (m, 2H), 1.670–1.776 (m, 4H), 1.905 (m, 2H), 2.464 (m, 1H), 3.157 (m, 2H), 3.567 (p, 2H).…”

Section: Methodsmentioning

confidence: 99%

Bimodal-hybrid heterocyclic amine targeting oxidative pathways and copper mis-regulation in Alzheimer's disease

et al. 2014

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Oxidative stress resulting from metal-ion misregulation plays a role in the development of Alzheimer’s disease (AD). This process includes the production of tissue-damaging reactive oxygen species and amyloid aggregates. Herein we describe the synthesis, characterization and protective capacity of the small molecule, lipoic cyclen, which has been designed to target molecular features of AD. This construct utilizes the biologically compatible and naturally occurring lipoic acid as a foundation for engendering low cellular toxicity in multiple cell lines, radical scavenging capacity, tuning the metal affinity of the parent cyclen, and results in an unexpected affinity for amyloid without inducing aggregation. The hybrid construct thereby shows protection against cell death induced by amyloid aggregates and copper ions. These results provide evidence for the rational design methods used to produce this fused molecule as a potential strategy for the development of lead compounds for the treatment of neurodegenerative disorders.

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“…Finally, the above-mentioned sulfonamides 5 were deprotected to give the corresponding primary amines 6 with excellent results, 16 by a protocol which implied the initial deprotonation of amide followed by a reductive cleavage of N-S bond through a naphthalene-catalyzed lithiation 17 reaction (Scheme 2). The whole process, N-alkylation of sulfonamide and deprotective reduction, is an interesting alternative to the direct monoalkylation of ammonia, which is a difficult task.…”

Section: Contents Lists Available At Sciencedirectmentioning

confidence: 99%