74746-15-9

Upstream product

• 2373-89-9 4,4'-dimethoxychalcone 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 696-62-8 para-iodoanisole 
• 123-11-5 4-methoxy-benzaldehyde 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 571-57-3 4-bromo-1-naphthol 
• 548796-75-4 1,1,3-tris(4-methoxyphenyl)prop-2-yn-1-ol 
• 768-60-5 4-methoxyphenylacetylen 
• 90-96-0 bis(p-methoxyphenyl)methanone 

Downstream Products

• 4356-69-8 1,1-bis-(4-methoxyphenyl)ethylene 

Relevant academic research and scientific papers

2,2,4,6-Tetraaryl-2H-benzo[h]chromenes: The influence of electronic communication between aryl substituents on their photochromism

A series of photochromic 2,2,4,6-tetraaryl-2H-benzo[h]chromenes have been efficiently synthesised by two complementary strategies employing the condensation of 1,1,3-triarylprop-2-yn-1-ols with 4-substituted 1-naphthols and Suzuki cross-coupling chemistry

Synthesis of arylated chalcone derivatives via palladium cross-coupling reactions

A useful protocol for arylation of the olefin double bond of chalcones to afford tri- and tetra-substituted chalcone derivatives is reported. The protocol begins with the Heck reaction between chalcones and aryl iodides providing β-arylchalcones. This reaction tolerates various functional groups on both rings, as well as deactivated aryl iodides. The products are obtained in moderate to excellent yields and the (E)-β-arylchalcones (E:Z > 96:4) can be isolated via precipitation. Competitive Heck reactions pointed to a significant effect of ring one substituents on the reaction rate, while substituents on ring two have a much smaller effect. To access α,β-diarylchalcones, a sequential bromination-Suzuki cross coupling strategy was applied to the β-arylated compounds which afforded double arylated chalcone derivatives in 60–99% yield over two steps.

The influence of a 1,1-diarylvinyl moiety on the photochromism of naphthopyrans

1,1,3-Triarylpent-4-en-1-yn-3-ols, efficiently obtained in two steps from 1,1,3-triarylprop-2-yn-1-ols by a Meyer-Schuster rearrangement and subsequent addition of lithium trimethylsilylacetylide, react with either a 1- or 2- naphthol to afford photochrom

Observations on the synthesis of photochromic naphthopyrans

1-Naphthol reacts with 1,1-diarylprop-2-yn-1-ols 5a,b, under alumina catalysis, by two pathways to give the photochromic naphtho[1,2-b]pyrans 6a,b, together with the propenylidenenaphthalenones 7a,b, representatives of a new class of merocyanine dyes. With 2-methyl-1-naphthol, formation of the photochrome is suppressed; the only products are merocyanines 7c,d. The cyclocondensation of 2-naphthol with 5a,b proceeds much more efficiently, to give the naphtho[2,1-b]pyrans 14a,b. Pyran formation is not suppressed from either 1-bromo- or 1-(4 -methoxyphenyl)-2-naphthol; reaction with 5a,b merely results in expulsion of the C-1 substituent. An alternative pathway supervenes in the reaction of 1-methyl-2-naphthol with 5a to give the benz[e]indanone 17, the constitution of which was determined by X-ray crystallography. Reaction of the 1,3,3-triarylpropynols 19a,b with 1-naphthol affords the naphthopyrans 20 together with merocyanines 21, whilst the isomeric pyrans 23 are efficiently produced from 2-naphthol. The configuration of merocyanines 7a and 21a was unequivocally established by X-ray crystallography. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Electrocyclic Reactions of Protonated Chalcones: Synthesis of 3-Arylindan-1-ones

A series of ortho-bromochalcones has been prepared and each has been heated and irradiated in strong acid.In most cases a four-electron electrocyclic reaction occurred preferentially to give 3-arylindan-1-ones in good yield.The acrylchalcone 4'-methoxy-3,