SYNTHESIS AND CYCLOPROPANATION OFE,EANDZ,Z-1,3-BIS(STYRYLSULFONYL)BENZENE

Abstract

The synthesis of 1,3-bis(styrylsulfonyI)benzene in two isomeric forms (Z. Z and E , E) and their cyclopropanation with dimethylsulfonium methylide has been described. The configurational assignments of these compounds have been made on the basis of IR, 'H NMR and ''C N M R spectral data.

Hydrothiolation of benzyl mercaptan to arylacetylene: application to the synthesis of (E) and (Z)-isomers of ON 01910·Na (Rigosertib®), a phase III clinical stage anti-cancer agent

“…Initially, we tested the effect of base on this hydrothiolation reaction. As we have used metallic sodium in ethanol or sodium hydroxide in ethanol in our earlier attempts to make ( Z )-vinyl sulfides, 31 the same approach was tried for this reaction. Both reactions (entries 1 and 2) did not proceed at reflux temperatures for more than 24 h. Alternatively, with a solid supported Al 2 O 3 /KF catalyst at 60 °C, this reaction proceeded to give a mixture of isomers ( Z / E = 56 : 44) with yields of less than 10%.…”

A novel donor–π–acceptor halochromic 2,6-distyrylnaphthalene chromophore: synthesis, photophysical properties and DFT studies

“…Crud product was filtered, dried and purified by column chromatography using petroleum ether and ethyl acetate elunt to obtain pure product (A) as a white solid (2.0 g, 81%). 46 1 H-NMR (250 MHz, CDCl 3 /TMS) δ (ppm): 3.65 (s, 6H), 7.48–7.95 (m, 3H). 13 C-NMR (62.5 MHz, CDCl 3 /TMS) δ (ppm): 47.9, 48.1, 126.8, 127.2, 135.1, 135.3, 140.8, 143.9.…”