3′,4′-Diphenyl-3H,4′H-spiro[benzo[b]thiophene-2,5′-isoxazol]-3-one

Abstract

The molecule of the title compound, C22H15NO2S, is built up from a benzothiophene system linked to an isoxazoline ring which is connected to two phenyl rings. The benzothiophene system is essentially planar, while the isoxazoline ring displays an envelope conformation with the spiro C atom as the flap. The mean plane through the isoxazoline ring is slightly inclined to one phenyl ring by 5.74 (13)° and is approximately perpendicular [86.10 (10)°] to the fused ring system and to the other phenyl ring [84.31 (12)°]. In the crystal, molecules are linked together by C—H...O hydrogen bonds and by π–π interactions between the fused ring systems [intercentroid distance = 3.702 (2) Å], forming a three-dimensional network.

Synthesis of new spiroheterocycles-fused isoxazoline from 2-arylidenes-3-phenyl-1-indanones through a regio-and diastereospecific 1,3-dipolar cycloaddition

“…NMR spectra of the crude product revealed the formation of only the regioisomer 3-phenyl-3',4'diaryl-4'H-spiro[indene-2,5'-isoxazol]-1(3H)-ones 3 (Scheme 1). The regiochemistry shown in this reaction was similar to the one obtained in reactions using other dipolarophiles [31][32][33][34][35][36][37] .…”

3′-(4-Chlorophenyl)-4′-phenyl-3H,4′H-spiro[benzo[b]thiophene-2,5′-isoxazol]-3-one

“…The 1,3-dipolar cycloaddition reaction of nitrile oxides to olefins is an efficient synthetic route to these heterocyclic systems in a one-pot reaction. In an extension of work in this area by our group (Bakhouch et al, 2014;Boughaleb et al, 2011), we have investigated the 1,3-dipolar cycloaddition reaction of nitrile oxides with thioaurones as the dipolarophile with an exocyclic double bond in order to determine if there were selectivity problems with cycloaddition reaction. We report herein the 1,3-dipolar cycloaddition reaction data reports between p-chlorobenzonitriloxide and (Z)-2-benzylidenebenzo [b]thiophen-3-one.…”