title: An entry into hexahydro-2H-thieno[2,3-c]pyrrole 1,1-dioxide derivatives.
abstract: Hexahydro-2H-thieno[2,3-c]pyrrole is proposed as a low molecular weight polar scaffold to construct compound libraries used in the search for new drugs. Practical syntheses of derivatives of this bicyclic scaffold were developed, based on [3 + 2] cycloaddition of the ylide generated from N-benzyl-1-methoxy-N-((trimethylsilyl)methyl)methanamine and 4-substituted 2,3-dihydrothiophene 1,1-dioxides. All of the 3-substituted hexahydro-2H-thieno[2,3-c]pyrrole 1,1-dioxide derivatives were obtained as single diastereomers. Conformational properties of the hexahydro-2H-thieno[2,3-c]pyrrole 1,1-dioxide derivatives were explored using X-ray diffraction studies. The potential of the scaffold to generate libraries of 3D-shaped molecules was demonstrated.
authors.affiliation: Kyiv National Taras Shevchenko University, Volodymyrska Street 60, Kyiv 01601, Ukraine.
authors.forename: Vladimir S
authors.initials: VS
authors.lastname: Yarmolchuk
authors.forename: Ivan L
authors.initials: IL
authors.lastname: Mukan
authors.forename: Oleksandr O
authors.initials: OO
authors.lastname: Grygorenko
authors.forename: Andrey A
authors.initials: AA
authors.lastname: Tolmachev
authors.forename: Svitlana V
authors.initials: SV
authors.lastname: Shishkina
authors.forename: Oleg V
authors.initials: OV
authors.lastname: Shishkin
authors.forename: Igor V
authors.initials: IV
authors.lastname: Komarov
mesh_terms: D003500:Cyclization; D008958:Models, Molecular; D015394:Molecular Structure; D011758:Pyrroles / Q000737:chemistry*; D013450:Sulfones / Q000737:chemistry; D014961:X-Ray Diffraction
chemical_list: D011758:Pyrroles; D013450:Sulfones