Modafinil (Diphenyl methyl Sulfinyl acetamid) is used clinically in the treatment of narcolepsy and sleeping disorders. The synthesis of R-modafinil, have started with the reaction of benzhydrol and thioglycolic acid in trifluoroacetic acid to afford benzhydryl sulfanyl acetic acid. The reaction of acid with thionyl chloride in benzene followed by treatment with ammonium hydroxide gave acetamid...

2-[(Diphenylmethyl)sulfinyl]acetamide (modafinil, (±)-1) is a unique dopamine uptake inhibitor that binds the dopamine transporter (DAT) differently than cocaine and may have potential for the treatment of psychostimulant abuse. To further investigate structural requirements for this divergent binding mode, novel thio- and sulfinylacetamide and ethanamine analogues of (±)-1 were synthesized whe...

New podand-type fluoroionophores having two pyrene moieties: 2,2´-bis(1-pyrenylacetyloxy)diphenyl sulfide (3), 2,2´-bis(1-pyrenylacetyloxy)diphenyl sulfoxide (4), and 2,2´-bis(1-pyrenylacetyloxy)diphenyl sulfone (5), have been synthesized by connecting two 1-pyrenecarbonylmethyl groups with the two hydroxy groups of 2,2´-dihydroxydiphenyl sulfide, sulfoxide, and sulfone, respectively. Their com...

In the title mol-ecule, C(15)H(17)IO(4)S, the O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment. In the crystal structure, inter-molecular I⋯O [2.994 (3) Å] halogen bonding links the mol-ecules into centrosymmetric dimers, which are further packed into ribbons along the c axis by inter-molecular sulfin-yl-sulfinyl inter-...

In the title compound, C(19)H(12)BrFO(2)S, the O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of the plane through the naphthofuran fragment. The 4-fluoro-phenyl ring is rotated out of the naphthofuran plane, making a dihedral angle of 41.65 (7)°. In the crystal, mol-ecules are linked by weak inter-molecular C-H⋯O and C-H⋯π inter-actions, and a short Br⋯F c...

There are two symmetry-independent mol-ecules in the asymmetric unit of the title compound, C(13)H(13)IO(4)S. In each mol-ecule, the O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment. The crystal structure is stabilized by aromatic π-π inter-actions between the benzene and furan ring [centroid-centroid distance = 3.866 (...

In the title compound, C(15)H(17)IO(4)S, the O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment. The crystal structure is stabilized by weak inter-molecular C-H⋯π inter-actions between a methyl H atom of the methyl-sulfinyl group and the benzene ring of the benzofuran system, and by an I⋯O halogen bond of 3.173 (3) Å and ...

The title compound, C(16)H(13)IO(2)S, was prepared by the oxidation of 2-(4-iodo-phen-yl)-5-methyl-3-methyl-sulfanyl-1-benzofuran with 3-chloro-peroxy-benzoic acid. The 4-iodo-phenyl ring makes a dihedral angle of 37.97 (9)° with the plane of the benzofuran fragment, and the O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of this plane. The mol-ecular packin...

We have synthesized a novel chiral NADH model compound, N-methyl-(R)-3-(tert-butyl)-sulphinyl-1,4-dihydropyridine with high enantioselectivity and used it in the reduction of methyl benzoylformate, producing (S)-methyl mandelate in 95% ee. The absolute structure of its precursor, 3-(tert-butyl)sulfinyl pyridine, was determined by X-ray analysis.

Synthesis of 4-aminotropones through a cyclization-ring expansion process occurs in a single step and with excellent yields from 4-amino-2,5-cyclohexadienones (p-quinamines) bearing a 4-sulfinyl or sulfonyl methyl group.