Synthesis of Benzoaryl-5-yl(2-hydroxyphenyl)methanones via Photoinduced Rearrangement of (E)-3-Arylvinyl-4H-chromen-4-ones

Abstract

A concise and efficient photoinduced rearrangement of (E)-3-arylvinyl-4H-chromen-4-ones for the synthesis of benzoaryl-5-yl(2-hydroxyphenyl)methanones is described. Benzoaryl-5-yl-(2-hydroxyphenyl)methanones were obtained in 77-95% yields via the irradiation of (E)-3-arylvinyl-chromones in the 95% EtOH with a high-pressure mercury lamp at room temperature under Ar atmosphere. The reported method provides a novel procedure for the synthesis of α,α'-diaryl ketone derivatives without addition of any transition metals and oxidants or other additives. A plausible mechanism was proposed, and the rearrangement product was characterized by NMR, HRMS, and X-ray.

Synthesis of (2-Aminophenyl)(naphthalen-2-yl)methanones via Intramolecular Rearrangement of (E)-3-Styrylquinolin-4(1H)-ones under Irradiation with 365 nm UV Light

“…CH 2 Cl 2 , MeCN, acetone, yielded 2a in only up to 27% yield (Table 1, entries 5-7). It is important to note that protic solvent 27 and acid 31 could significantly improve the rearrangement efficiency, which is consistent with the references. 27,31 Interestingly, addition of water could slightly boost the yield of 2a (66-70%, Table 1, entries 8-10).…”

“…It is important to note that protic solvent 27 and acid 31 could significantly improve the rearrangement efficiency, which is consistent with the references. 27,31 Interestingly, addition of water could slightly boost the yield of 2a (66-70%, Table 1, entries 8-10). However, a low-er yield of 2a was observed with increased concentration of 1a (1 × 10 -2 mol/L, 52%, Table 1, entry 11).…”

“…Recently, the synthesis of benzoaryl-5-yl(2-hydroxyphenyl)methanones via the photoinduced rearrangement of (E)-3-arylvinyl-4H-chromen-4-ones in high yields was reported. 27 Scheme 2 Synthesis of (2-aminophenyl)(naphthalen-2-yl)methanones via the photoinduced rearrangement of (E)-3-styrylquinolin-4(1H)-ones…”

Synthesis of Trans‐4a,12b/3,4‐Dihydrodibenzo[f,h]quinolin‐2(1H)‐Ones and Dibenzo[f,h]quinolin‐2(1H)‐Ones via Irradiation of 6‐Biphenylpyridine‐2(1H)‐Ones

“…[14,15] The (2-hydroxyphenyl)-(fusedphenyl)-methanones and benzoaryl-5-yl(2-hydroxyphenyl)methanones were synthesized via the photo-induced rearrangement of 2-arylisoflavones, (E)-3-arylvinyl-4H-chromen-4-ones. [16,17] Following our interest, we would like to demonstrate the synthesis of trans-4a,12b-dihydrodibenzo[f,h]quinolin-2(1H)-ones 2, dibenzo[f,h]quinolin-2(1H)-ones 3, and 3,4-dihydrodibenzo[f,h]quinolin-2(1H)-ones 4 via the irradiation of 6-([1,1'-biphenyl]-2-yl)pyridin-2(1H)-ones 1 with a 313 nm lamp under different conditions (Scheme 2). Solution of 1 in 1,4-dioxane was irradiated with a 313 nm UV light at ambient temperature under Ar atmosphere for 3 h to give photo-induced rearrangement product 2.…”

Visible-Light-Induced C–C Coupling Reaction to Synthesize Bipyridine From 3-Cyano-1,4-Dihydropyridines

“…Photocatalysis has developed significantly over the past decade, making possible synthetic transformations that were previously impossible (Ravelli et al, 2016;Romero and Nicewicz, 2016;She et al, 2018). The photochemical reaction does not require additional additives or reagents, thus embodying the concept of green chemistry (Norbert, 2008;Fan et al, 2017). To date, photochemical reactions have been applied to various fields of organic chemistry as ecofriendly and efficient synthesis method, including metal catalysis (Condie et al, 2010), green organic synthesis (Yu et al, 2018), total synthesis (Reddy and Rawal, 2000) and asymmetric synthesis (Richard et al, 2015) of compounds.…”