Crystal structure of 3,4′-diphenyl-3′-p-tolyl-4′H-spiro[indan-2,5′-[1,2]oxazol]-1-one

Abstract

In the title compound, C30H23NO2, the five-membered rings are both in envelope conformations with the same spiro C atom as the flap. The benzene ring and the two phenyl rings are inclined to the mean plane of the indene ring system by 83.98 (8), 81.46 (8) and 72.31 (7)°. In the crystal, mol­ecules are linked by pairs of C—H⋯O hydrogen bonds into inversion dimers. The dimers are further connected by C—H⋯N inter­actions, forming layers parallel to (10-1).

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] .…”

“…The structure of cycloadduct 3b, whose crystallographic data have been previously published 31 , was corroborated by X-ray single-crystal diffraction (Figure 2). This structural determination confirms the resulting regiospecificity and diastereospecificity.…”

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

“…Among these compounds, spiroisoxazolines have shown strong bioactivities (Bennani et al, 2007;Al Houari et al, 2008;Hwang et al, 2005). For many years, our laboratory has accumulated much experience in the design and synthesis of heterocyclic systems with isoxazoline and pyrazoline rings through 1,3-dipolar cycloaddition and cyclocondensation reactions (El Yazidi et al, 2003;Bakhouch et al, 2014Bakhouch et al, , 2015Bakhouch et al, , 2017Mahfoud et al, 2015). In a continuation of our previous work, and in an attempt to evaluate the reactivity of thioaurones with nitrile oxides as a dipole (Boughaleb et al, 2011), we describe herein the reaction of (Z)-2-benzylidenbenzo[b]thiophen-3(2H)-one with benzonitrile oxide in chloroform at low temperature.…”

2-Methyl-3′-(4-methylphenyl)-4′-(2-nitrophenyl)-4′H-spiro[chroman-3,5′-isoxazol]-4-one

“…Spiroisoxazolines have various biological properties such as herbicidal (De Amici et al, 1990)and plant-growth regulatory activities (Howe & Shelton, 1990) and have applications as antitumor agents (Smietana et al, 1999) and anti-HIV agents (Liu et al, 1997). In this work we have studied the regio-and stereoselective synthesis of spiroisoxazoline 2-methyl-4 0 -(nitrophenyl)-3 0 -(p-tolyl)-4 0 H-spiro[chroman-3,5 0 -isoxazol]-4-one obtained by the 1,3-dipolar cycloaddition (Mahfoud et al, 2015, Boughaleb et al, 2011 of (E)-2methyl-3-(4-nitrobenzylidene)chroman-4-one and 4-tolylbenzonitrile oxide. This concerted reaction affords a single regio-isomer which is the trans-spiroisoxazoline data reports (Bakhouch et al, 2014).…”