Efficient and Stereoselective Syntheses of Isomerically Pure 4-Aminotetrahydro-2H-thiopyran 1-Oxide Derivatives

Abstract

Efficient and stereoselective syntheses of isomerically pure 4-aminotetrahydro-2H-thiopyran 1-oxide derivatives have successfully been achieved. Isomerically pure (4-nitrophenyl)­sulfonyltetrahydro-2H-thiopyran 1-oxides were identified by X-ray crystallographic analyses, and isomerically pure sulfoxide derivatives were characterized by 1H NMR. An oxidation reaction of tert-butyl­(4-nitrophenyl)­sulfonyl­(tetrahydro-2H-thiopyran-4-yl)­carbamate with Oxone provided steric control, affording its trans sulfoxide with high efficiency and selectivity. From the obtained trans sulfoxide derivatives, cis sulfoxide derivatives were synthesized conveniently by a hydrogen chloride catalyzed isomerization.

Application of Nanomagnetic NH 2 .MIL-101(Fe)/ED as a Retrievable and Efficient Catalyst for the Synthesis of 2,6-Diamino-4-Aryl-4H-Thiopyran- 3,5- Dicarbonitrile Derivatives

“…As shown in Table 2, not using a catalyst was resulted in low yield of the nal product (entries 1-5). Also, the use of catalyst components separately provided a moderate yield of the desired product (entries [13][14][15][16][17][18]. In contrast, it is noteworthy that a cosiderable amount of 5a was formed in the presence of magnetic NH 2 .MIL-101(Fe)/ED after 30 min in a smooth, meaningful manner (entry 11).…”

“…[6][7][8][9][10][11][12][13] Among the S-heterocycles, thiopyran frameworks are known as maneuverable skeletons and therefore have been subject to extensive study due to their unique properties such as the anticancer, and antimicrobial activities. [14][15][16][17][18][19][20][21][22][23] Meanwhile, tricyclic thiopyran-2-one compounds are of use in the therapies for the treatment of viral infections and diseases including AIDS which further emphasize that these organic skeletons are likely to be of considerable practical signi cance. 24 Hence, chemists are hunting new ways to create various S-heterocycles and therefore a great deal of synthetic ways have been developed for the construction of these structures.…”

Facile one-pot, multi-component reaction to synthesize spirooxindole-annulated thiopyran derivatives under environmentally benevolent conditions

“…Among the S -containing heterocyclic compounds, thiopyran scaffolds have been carefully examined by scientists, and studies have validated their notable features, such as antiviral and antimicrobial properties. Moreover, one of the striking features of these motifs is their application in the treatment of cancer [ 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 ]. In consequence, chemists are hunting new ways to create various thiopyran-containing heterocycles.…”