An effective synthesis of fused cyclic thiopyrans and pyrans by molybdenum(VI) sulfide catalyzed reduction of the corresponding thiopyranones and pyranones
- Resource Type
- Authors
- Yuzuru Takagi; Kunio Itabashi; Toshio Takido
- Source
- Journal of Heterocyclic Chemistry. 32:687-690
- Subject
- chemistry.chemical_classification
Sulfide
Dihydropyran
Organic Chemistry
chemistry.chemical_element
Selective catalytic reduction
Carbonyl group
Catalysis
chemistry.chemical_compound
chemistry
Pyran
Molybdenum
Hydrogenolysis
Organic chemistry
- Language
- ISSN
- 1943-5193
0022-152X
The synthesis of fused cyclic dihydrothiopyrans 2a-c from dihydrothiopyranones 1a-c and thiopyrans 2d-f from thiopyranones 1d-f by catalytic reduction over molybdenum(VI) sulfide (MoS3) has been studied. The hydrogenolysis of the carbonyl group of 1a-f over MoS3 catalyst proceeded selectively to give the corresponding 2a-f in high yields. Neither alcohols nor olefins were not detected in the products. The method was also applied successfully to the synthesis of dihydropyran 2h and pyran 2g from dihydro-pyranone 1h and pyranone 1g.