engleski

Chemistry of 1, 3-Dioxepins. XVI. The Synthesis, Characterization and Crystallographic Analysis of Some Arylsulphanyl-, Arylsulphinyl, Arylsulphonyl- and Benzoyl- N-Substituted Derivatives of 1a, 2, 6, 6a-Tetrahydro-1H, 4H-[1, 3]dioxepino[5, 6-b]azirines

Chemo-selective synthesis and characterization of of N-[(4-nitrophenyl)sulphanyl]- 2 and N-[(4-nitrophenyl)sulphinyl]- 3 N-[(4-aminophenyl)sulphonyl]- 5 and N-(4-aminobenzoyl)- 7 derivatives of 1a, 2, 6, 6a-tetrahydro-1H, 4H-[1, 3]dioxepino[5, 6-b]azirines, starting from 1a, 2, 6, 6a-tetrahydro-1H, 4H-[1, 3]dioxepino[5, 6-b]azirine (1), are described. Their solid state conformational behaviour based on crystallographic analysis shows that: • dioxepinoazirine moiety of 3, 5 and 7 adopts a boat-chair (BC) conformation, while dioxepinoaziridine moiety of 3 adopts a twist-boat (TB) conformation • the substituent on aziridine nitrogen is always in trans and never in cis position in relation to the dioxepane ring, • the orientation of sulphanyl-, sulphinyl- sulphonyl- and carbonyl- moiety in 2, 3, 5 and 7 are defined by torsion angles C1-S1-N1-C7 of 110.7(2)°, 82.6(2)°, 88.80(11)°and C1-C-N1-C7 of 64.9(5)°, respectively, • Phenyl moiety of sulphinyl and sulphonyl derivatives, 3 and 5 is perpendicular to S-N bond with the torsion angles N1-S1-C1-C2 of 67.9(3)° and -92.54(13)°, respectively, while that one of sulphanyl- 2 and carbonyl- 7 derivatives is coplanar to S-N or C-N bonds with the torsion angles N1-S1-C1-C2 and N1-C-C1-C2 of 168.5(2)° and 170.9(4)°, respectively. Obtained data will serve for further investigation of steric and electronic properties of studied compounds directed toward design of antihyperglycaemicaly more potent analogues.

1 ; 3-Dioxepins ; 1a ; 2 ; 6 ; 6a-tetrahydro-1H ; 4H-[1 ; 3]dioxepino[5 ; 6-b]azirines ; sulphanyl- ; sulphinyl- ; crystallographic analysis ; conformational behaviour ; antihyperglycaemics

nije evidentirano