Unusual cyclodimerization of small cyclic ethers via neighboring carbonyl-group participation and cation transfer

Kanoh, Shigeyoshi; Nishimura, Toshiaki; Naka, Masashi; Motoi, Masatoshi

doi:10.1016/s0040-4020(02)00702-0

Cited by 6 publications

(2 citation statements)

References 25 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Preparation of 3-oxetane 24 (Scheme ) was initiated via transformation of aldehyde 20 to triol 21 via Tollens condensation . Cyclization of 21 followed by oxidation of resulting alcohol 22 to aldehyde 23 and subsequent reaction with pyridyl-2-lithium generated final compound 24 . Nitrogen analogues of 24 , azetidines 29a , b , were synthesized from cyanoazetidine intermediate 25 (Scheme ).…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and Pharmacology of (Pyridin-2-yl)methanol Derivatives as Novel and Selective Transient Receptor Potential Vanilloid 3 Antagonists

et al. 2016

View full text Add to dashboard Cite

Transient receptor potential vanilloid 3 (TRPV3) is a Ca(2+)- and Na(+)-permeable channel with a unique expression pattern. TRPV3 is found in both neuronal and non-neuronal tissues, including dorsal root ganglia, spinal cord, and keratinocytes. Recent studies suggest that TRPV3 may play a role in inflammation, pain sensation, and skin disorders. TRPV3 studies have been challenging, in part due to a lack of research tools such as selective antagonists. Herein, we provide the first detailed report on the development of potent and selective TRPV3 antagonists featuring a pyridinyl methanol moiety. Systematic optimization of pharmacological, physicochemical, and ADME properties of original lead 5a resulted in identification of a novel and selective TRPV3 antagonist 74a, which demonstrated a favorable preclinical profile in two different models of neuropathic pain as well as in a reserpine model of central pain.

show abstract

Section: Chemistrymentioning

confidence: 99%

Synthesis and Pharmacology of (Pyridin-2-yl)methanol Derivatives as Novel and Selective Transient Receptor Potential Vanilloid 3 Antagonists

et al. 2016

View full text Add to dashboard Cite

show abstract

“…The preferred ring sizes formed are three-, five-, and six-membered rings [196][197][198][199][200], although a few examples of four- [201] and seven-membered [202] [193][194][195]. The preferred ring sizes formed are three-, five-, and six-membered rings [196][197][198][199][200], although a few examples of four- [201] and seven-membered [202] [193][194][195].…”

Section: Neighboring-group Participationmentioning

confidence: 99%

Aliphatic Nucleophilic Substitutions: Problematic Electrophiles

Dörwald

2004

Side Reactions in Organic Synthesis

View full text Add to dashboard Cite

Nucleophilic substitutions at sp 3 -hybridized carbon are among the most useful synthetic transformations, and have been thoroughly investigated [1][2][3]. The success of these reactions depends mainly on the structures of the nucleophile and electrophile, their concentration, and on the solvent and reaction temperature chosen. The structure of the electrophile in nucleophilic substitutions is of critical importance, because many unwanted side reactions result from unexpected reactivity of the electrophile.In Scheme 4.1 the mechanisms of typical monomolecular (Sn1) and bimolecular (Sn2) nucleophilic substitutions at a neutral electrophile with an anionic nucleophile are sketched. Sn1 reactions usually occur when the electrophile is sterically

show abstract