Cumhur Kirilmis

Synthesis, Reactivity and Biological Activity of Novel Bisbenzofuran-2-yl-Methanone Derivatives

Preparation of bisbenzofuran-2-yl-methanone (1), the corresponding ketoxime 4, semicarbazone and thiosemicarbazone 3a and 3b, ether derivatives of the ketoximes 5a-j and the alcohol 2 are described. These substances have been prepared in excellent yields. All the synthesized compounds except 5i have been tested against five different microorganisms and some of them were found to be active against some of the species studied.

C—H⋯O, C—H⋯π and π–π inter­actions in three benzofuran-2-yl ketone derivatives

The molecules of 2-benzoyl-l-benzofuran, C 15 H 10 O 2 , (I), interact through double C-H...O hydrogen bonds, forming dimers that are further linked by C-H...O, C-H...π and π-π interactions, resulting in a three-dimensional supramolecular network. The dihedral angle between the benzoyl and benzofuran fragments in (I) is 46.15 (3)°. The molecules of bis(5-bromo-1-benzofuran-2-yl) ketone, C 17 H 8 Br 2 O 3 , (II), exhibit C 2 symmetry, with the carbony] group (C=O) lying along the twofold rotation axis. and are linked by a combination of C-H...O and C-H...π interactions and Br...Br contacts to form sheets. The stability of the molecular packing in 3-mesityl-3-methylcyclobutyl 3-methylnaphtho[1,2-b]furan-2-yl ketone, C 28 H 28 O 2 , (III), arises from C-H...π and 7r-7r stacking interactions. The fused naphthofuran moiety in (III) is essentially planar and makes a dihedral angle of 81.61 (3)° with the mean plane of the trimethylbenzene ring.