Original scientific paper

Chemistry of 1,3-Dioxepins. XVI.1 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

Biserka Prugovečki
Marina Marinković
Mladen Vinković
Miljenko Dumić

Abstract

Chemo-selective synthesis and characterization 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: (i) dioxepinoazirine moiety of 2, 5 and 7 adopts a boat-chair (BC) conformation, while dioxepinoaziridine moiety of 3 adopts a twistboat
(TB) conformation; (ii) the substituent on aziridine nitrogen is always in trans and never in cis position in relation to the dioxepane ring; (iii) the orientation of sulphanyl-, sulphinylsulphonyl- 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; (iv) Phenyl moiety of sulphinyl and sulphonyl derivatives, 3 and 5, is perpendicular to the S-N bond with the torsion
angles N1-S1-C1-C2 of 67.9(3)° and –92.54(13)°, respectively, while that 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 aimed at designing antihyperglycaemically
more potent analogues.

Keywords

chemo-selective synthesis; chemo-selective synthesis; 1,3-dioxepins; 1a,2,6,6a-tetrahydro-1H,4H-[1,3]-dioxepino[5,6-b]azirines; sulphanyl; sulphinyl; crystallographic analysis; conformational behaviour; antihyperglycaemics

Hrčak ID:

4152

URI

https://hrcak.srce.hr/4152

Publication date:

19.7.2006.

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