Thallium in organic synthesis. 57. Reaction of chalcones and chalcone ketals with thallium(III) trinitrate

Oxidative rearrangement of chalcones without a hydroxy group by thallium(III) nitrate in methanol

“…Although the 'H NMR spectral pattern for the propanoate P3g obtained here is greatly different from that for methyl 3methoxy-2-(4-methoxyphenyl)-3-phenylpropanoate P6a synthesized from 4'-methoxychalcone 6a by Taylor et a1., 6 but similar to that for compound A3g (see Table 4), the structure of compound P3g can be confirmed as methyl 3-(4-chlorophenyl)-2-(2,4-dimethyoxphenyl)-3-methoxypropanoate from the following facts. In a nuclear Overhauser enhancement WOE) experiment on ester P3g, the NOE (1 1 and 20%) of the doublet at 6 4.58 and the aromatic proton signal at 6 6.14 were observed by irradiation of the singlets at 6 3.22 and 3.38, respectively, and that of the doublet at 6 4.36 was not observed by irradiation of the other methoxy signals.…”

Benzils: A Review on their Synthesis

“…In the recent decades, considerable work was carried out in oxidative rearrangements for the synthesis of benzils 1 . Amongst them, α , β ‐unsaturated diaryl ketones or chalcones 109 was one of the substrates investigated in the early 1970s by McKillop [161] & Taylor [162] for the synthesis of benzils 110 . Thallium(III) nitrate (TTN) was used as an oxidant in perchloric acid medium (Scheme 50).…”

Synthesis and biological evaluation of α, β-unsaturated ketone as potential antifungal agents

“…All the compounds synthesized were characterized spectroscopically Optical density of positive control and negative control was 0.35 and 0.01, respectively f Basaif et al (2005), g Dhar (1972), h Taylor et al (1980), i Goto et al (1991) Procedures for the synthesis of 1-(5-bromothiophen-2-yl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one (16) 3,4-Dimethoxybenzaldehyde (0.25 g, 0.0015 mol) was reacted with 2-acetyl-5-bromothiophene (0.189 g, 0.0015 mol) using the general procedure to obtain chalcone 16 ( 56.024, 110.165, 111.127, 118.296, 122.439, 123.368, 127.486, 131.293, 131.506, 144.766, 142.274, 149.255, 151.663, 180.847 Procedures for the synthesis of 3-(biphenyl-4-yl-1-(5-bromothien-2-yl)-)prop-2-en-1-one (18) Biphenyl-4-carboxaldehyde (0.25 g, 0.00137 mol) was reacted with 2-acetyl 5-bromothiophene (0.28 g, 0.00137 mol) using the general procedure to obtain chalcone 18 ( …”

“…Thus, in this study, various compounds were synthesized and tested for antifungal activity. Some of these chalcones have been reported earlier; however they have not been screened for antimicrobial activity (Hayashi et al, 1989;Tafi et al, 2002;Joo et al, 2003;Sivakumar et al, 2007;Meng et al, 2004;Basaif et al, 2005;Dhar, 1972;Taylor et al, 1980;Goto et al, 1991). The general scheme is shown in Scheme 1.…”