Naslov
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

Autori
Prugovečki, Biserka ; Marinković, Marina ; Vinković, Mladen ; Dumić, Miljenko

Izvornik
Croatica chemica acta (0011-1643) 79 (2006), 2; 219-226

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

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

Sažetak
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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA