Some Ethers Derived from Diethylaminoethyl Benzilate

Antileishmanial Chalcones: Statistical Design, Synthesis, and Three-Dimensional Quantitative Structure−Activity Relationship Analysis

“…2-Butoxy-2 ‘ ,3 ‘ ,4 ‘ -trimethoxychalcone (27) was synthesized according to procedure E using 2-butoxybenzaldehyde (1.7 g, 9.5 mmol) and 2,3,4-trimethoxyacetophenone (1.7 mL, 9.5 mmol) as starting materials: yellow crystals (3.0 g, 86%); mp 129.4−130.2 °C (ethanol−water); 1 H NMR (CDCl 3 ) 8.04 (d, J = 16.0 Hz, Hβ), 7.62 (dd, J = 7.7, 1.5 Hz, H6), 7.55 (d, J = 16.0 Hz, Hα), 7.46 (d, J = 8.8 Hz, H6‘), 7.31 (td, J = 7.7, 1.5 Hz, H4), 6.94 (bt, J = 7.7 Hz, H5), 6.89 (bd, J = 7.7 Hz, H3), 6.74 (d, J = 8.8 Hz, H5‘), 4.00 (t, J = 6.4 Hz, H1‘‘), 3.97 (s, OCH 3 ), 1.80 (pent, J = 7.4 Hz, H2‘‘), 1.48 (hext, J = 7.4 Hz, H3‘‘), 0.96 (t, J = 7.3 Hz, H4‘‘); 13 C NMR (CDCl 3 ) 191.4 (CO), 157.8 (C2), 156.3 (C4‘), 153.1 (C2‘), 141.6 (C3‘), 138.7 (Cβ), 131.2 (C4), 128.4 (C6), 126.6 (C1), 126.5 (Cα), 125.2 (C6‘), 123.6 (C1‘), 120.1 (C5), 111.7 (C3), 106.8 (C5‘), 67.7 (C1‘‘), 61.7 (OCH 3 ), 60.6 (OCH 3 ), 55.7 (OCH 3 ), 30.8 (C2‘‘), 19.0 (C3‘‘), 13.5 (C4‘‘). Anal.…”

“…3,5-Dimethoxy-4′-cyclohexylchalcone (23) was synthesized according to procedure E using 3,5-dimethoxybenzaldehyde (0.82 g, 4.9 mmol) and 4-cyclohexylacetophenone (1.0 g, 4.9 mmol) as starting materials: brown crystals (1.6 g, 92%); mp 75.5-76.2 °C (ethanol-water); 1 H NMR (CDCl3) 7.95 (m, H2′ and H6′), 7.64 (d, J ) 15.9 Hz, Hβ), 7.48 (d, J ) 15.9 Hz, HR), 7.33 (m, H3′ and H5′), 6.78 (d, J ) 2.2 Hz, H2, H6), 6.52 (t, J ) 2.2 Hz, H4), 3.84 (s, OCH3), 2.58 (b, H1′), 1.8 (m, H2′′, H6′′), 1.4 (m, H3′′-H5′′); 13 2-Butoxy-2′,3′,4′-trimethoxychalcone (27) was synthesized according to procedure E using 2-butoxybenzaldehyde 40 (1.7 g, 9.5 mmol) and 2,3,4-trimethoxyacetophenone (1. 7 2-Nitro-2′,3′,4′-trimethoxychalcone (29) was synthesized according to procedure F using 2-nitrobenzaldehyde (0.72 g, 4.8 mmol) and 2,3,4-trimethoxyacetophenone (0.8 mL, 4.8 mmol) as starting materials: red-brown crystals (0.22 g, 13%); mp 107.1-108.0 °C (ethanol-water); 1 H NMR (CDCl3) 8.04 (d, J ) 15.7 Hz, Hβ), 8.03 (dd, J ) 8.0, 1.2 Hz, H3), 7.76 (dd, J ) 7.8, 1.7 Hz, H6), 7.67 (td, J ) 7.8, 1.2 Hz, H5), 7.55 (td, J ) 8.0, 1.8 Hz, H4), 7.53 (d, J ) 8.8 Hz, H6′), 7.37 (d, J ) 15.7 Hz, HR), 6.79 (d, J ) 8.8 Hz, H5′), 3.94 (s, OCH 3), 3.92 (s, OCH3), 3.91 (s, OCH3); 13 2-Fluoro-2′,3′,4′-trimethoxychalcone (30) was synthesized according to procedure E using 2-fluorobenzaldehyde (1.7 mL, 16.1 mmol) and 2,3,4-trimethoxyacetophenone (2.9 mL, 16.1 mmol) as starting materials: white crystals (3.6 g, 81%); mp 75.0-75.8 °C (ethanol-water); 1 H NMR (CDCl3) 7.82 (d, J ) 16.0 Hz, Hβ), 7.64 (td, J ) 7.6, 1.4 Hz, H4), 7.62 (d, J ) 16.0 Hz, HR), 7.52 (d, J ) 8.8 Hz, H6′), 7.35 (m, H6), 7.17 (bt, J ) ∼8 Hz, H5), 7.10 (bt, J ) ∼8 Hz, H3), 6.77 (d, J ) 8.8 Hz, H5′), 3.96 (s, OCH 3), 3.94 (s, OCH3), 3.91 (s, OCH3); 13 3-Phenoxy-2′,3′,4′-trimethoxychalcone (31) was synthesized according to procedure E using 3-phenoxybenzaldehyde (0.82 mL, 4.8 mmol) and 2,3,4-trimethoxyacetophenone (0.87 mL, 4.8 mmol) as starting materials: yellow crystals (1.1 g, 58%); mp 63.3-64.0 °C (ethanol-water); 1 H NMR (CDCl3) 7.63 (d, J ) 15.8 Hz, Hβ), 7.48 (d, J ) 8.8 Hz, H6′), 7.45 (d, J ) 15.8 Hz, HR), 7.4-7.0 (m, H2, H3, H6, H5′, H3′′-H5′′), 7.12 (t, J ) 7.8 Hz, H5), 7.02 (m, H2′, H6′′), 3.91 (s, OCH3), 3.87 (s, OCH3); 13 C NMR (CDCl3) 190.2 (CdO), 157.6 (C3, C1′′), 157.0 (C4′), 156.4 (C2′), 141.8 (Cβ), 137.6 (C3′) 136.7 (C1), 130.0 (C5), 129.6 (C3′′), 126.9 (CR), 126.2 (C1′), 125.7 (C6′), 123.4 (C4′′), 123.1 (C6), 120.1 (C4), 118.9 (C2′′), 117.6 (C2), 107.1 (C5′), 61.7 (OCH 3), 60.8 (OCH3), 55.9 (OCH3).…”

Direct Construction of 4-Hydroxybenzils via Para-Selective C–C Bond Coupling of Phenols and Aryl Methyl Ketones

“…As a testament to the utility of this method, target-oriented compounds were specified. The pharmaceutical candidate NSC 115566 , which is considered difficult to synthesize, can be obtained from the reaction between simple acetophenone and phenol under our conditions, followed by an alkylation reaction, in 47% overall yield (Scheme ). Moreover, this coupling reaction has definite potential to open up new vistas in the total synthesis of 4-hydroxybenzil natural products.…”