Topic
Thiane
About: Thiane is a research topic. Over the lifetime, 123 publications have been published within this topic receiving 1338 citations.
Papers published on a yearly basis
Papers
TL;DR: In this paper, a visible light-mediated ring contraction of α-acylated saturated heterocycles is described, which is orthogonal to traditional ring contractions, challenging the paradigm for diversification of heterocyclic compounds.
Abstract: Saturated heterocycles are found in numerous therapeutics and bioactive natural products and are abundant in many medicinal and agrochemical compound libraries. To access new chemical space and function, many methods for functionalization on the periphery of these structures have been developed. Comparatively fewer methods are known for restructuring their core framework. Herein, we describe a visible light-mediated ring contraction of α-acylated saturated heterocycles. This unconventional transformation is orthogonal to traditional ring contractions, challenging the paradigm for diversification of heterocycles including piperidine, morpholine, thiane, tetrahydropyran, and tetrahydroisoquinoline derivatives. The success of this Norrish type II variant rests on reactivity differences between photoreactive ketone groups in specific chemical environments. This strategy was applied to late-stage remodeling of pharmaceutical derivatives, peptides, and sugars.
124 citations
113 citations
TL;DR: The 13C and 17O (natural abundance) chemical shifts of several mono-and di-methyl ring-substituted thiane 1-oxides and thian 1,1-dioxides are reported in this paper.
Abstract: The 13C and 17O (natural abundance) chemical shifts of several mono- and di-methyl ring-substituted thiane 1-oxides and thiane 1,1-dioxides are reported. The cis and trans isomers of methyl-substituted thiane 1-oxide are readily identified by 13C and 17O NMR. In particular, the 17O NMR signals of axial SO groups are found several ppm upfield of those of the equatorial counterparts. The proportion of axial and equatorial conformers of thiane 1-oxide in different solvents has been measured by low-temperature 13C NMR. In THF the proportion of the axial conformer is higher than in CD2Cl2 whereas in CDCl3 or CHF2Cl the conformational preference is reversed and the equatorial conformer is slightly favoured.
43 citations
TL;DR: The synthesis and biological activity of trans-(+-)-N-methyl-2-(3-pyridyl)-2-tetrahydrothiopyrancarbothioamid+ ++ e 1-oxide and analogues is reported, which constitute a new structural class of K(+)-channel opener.
Abstract: The synthesis and biological activity of trans-(+-)-N-methyl-2-(3-pyridyl)-2-tetrahydrothiopyrancarbothioamid+ ++ e 1-oxide (8a, RP 49356) and analogues is reported. These compounds constitute a new structural class of K(+)-channel opener. The effects of changes in pyridyl group, thioamide, and thiane ring on in vitro K(+)-channel opening reactivity are discussed. A 3-pyridyl or 3-quinolyl group, a small N-alkyl thioamide function, and a thiane oxide ring, in which the sulfoxide is in a trans relationship to the thioamide, are preferred for activity. Selected compounds were tested intravenously in the normotensive anaesthetized rat for hypotensive effects, and the activities reflect their in vitro K(+)-channel opening activity. This led to further evaluation of compound 8a and the selection of the (-)-enantiomer 8b (RP 52891) for development as an antihypertensive and antianginal agent.
41 citations
Related Topics (5)
Performance Metrics
| Year | Papers |
|---|---|
| 2021 | 1 |
| 2020 | 2 |
| 2019 | 3 |
| 2016 | 3 |
| 2015 | 4 |
| 2014 | 2 |