2-r-(4-Chlorophenyl)-6-c-phenyl-3,4,5,6-tetrahydro-2H-thiopyran-4-one 1-oxide

Abstract

The thio­pyran unit of the title mol­ecule, C17H15ClO2S, is in chair form. A crystallographic mirror plane bis­ects the mol­ecule, passing through the O=S and the opposite C=O atoms of the central ring, with statistical disorder of the Cl atom. The geometry around the S atom is tetra­hedral and the carbonyl C is planar. The 4-chloro­phenyl group at the 2 position and the phenyl ring at the 6 position have equatorial orientations. Inter­molecular C—H⋯O and C—H⋯Cl hydrogen bonds are found in the crystal structure. In addition, there is a short O⋯C inter­molecular contact [2.970 (5) Å].

Chemoselective Synthesis and Anti-Kinetoplastidal Properties of 2,6-Diaryl-4H-tetrahydro-thiopyran-4-one S-Oxides: Their Interplay in a Cascade of Redox Reactions from Diarylideneacetones

“…NMR and LCMS analyses were fine for sulfoxide for both products. Further to previous studies [42][43][44], the NMR spectra of the major isomer agree with an axial configuration of the sulfoxide.…”

“…NMR and LCMS analyses were fine for sulfoxide for both products. Further to previous studies [42][43][44], the NMR spectra of the major isomer agree From a stereochemistry point of view, the oxidation of the cis sulfide should give two different diastereoisomers, depending on the position of the oxygen. In one case, it is in an equatorial position (hereafter quoted as anti-cis sulfoxide isomer), whereas in the other case, it is in an axial position (hereafter quoted as syn-cis sulfoxide isomer) (Figure 1).…”

“…NMR and LCMS analyses were fine for sulfoxide for both products. Further to previous studies [42][43][44], the NMR spectra of the major isomer agree The most stable configuration of the sulfoxide for this kind of heterocycle has been discussed in several studies [42,50,51]. According to these works, the axial position is surprisingly more stable than the equatorial one; the syn-cis is therefore expected to be the major isomer, if not the unique one.…”

“…To our knowledge, the synthesis of 2,6-DA-4-THTP sulfoxides derivatives has been described in only three articles, which were limited to the oxidation of the cis isomer [42][43][44]. In each case, wet bromine was used to oxidize the sulfur, with a variable yield of up to 83%.…”