Synthesis of novel substituted diaryl-1,4-diazepines

Abstract

In this paper a convenient route to new 2,3-diaryl-substituted 1,4-diazepines is described through cyclization of ethanedione derivatives and 1,3-propanediamine. The ethanedione derivatives required were synthesized by microwave-assisted oxidation from ethanones.

Visible-Light-Mediated α-Arylation of Enol Acetates Using Aryl Diazonium Salts

“…This interest arises from the importance of α-aryl carbonyl moieties in many pharmaceuticals and bioactive molecules, including well-known drugs such as ibuprofen and the β-blocker atenolol. 1,2-Diarylated ethanones (deoxybenzoines) can serve as valuable building blocks for the synthesis of heterocycles such as oxazoles, pyrazoles, diazepines, and indoles, which are common functionalities in various drug molecules.…”

Selectfluor-Mediated Simultaneous Cleavage of C–O and C–C Bonds in α,β-Epoxy Ketones Under Transition-Metal-Free Conditions: A Route to 1,2-Diketones

“…Purified by column chromatography (petroleum ether/EtOAc, 10:1) as a pale yellow solid (52.7 mg, 77%); mp 64–66 °C (lit . mp 66–68 °C); IR (KBr) ν 1667 (CO) cm –1 ; 1 H NMR (CDCl 3 , 500 MHz) δ 8.04 (dd, J 1 = 9.0 Hz, J 2 = 5.5 Hz, 2H), 7.99 (d, J = 7.5 Hz, 2H), 7.69 (t, J = 7.5 Hz, 1H), 7.54 (t, J = 8.0 Hz, 2H), 7.21 (t, J = 8.5 Hz, 2H); MS (EI, 70 eV) m / z (%) 228 (3) [M + ], 105 (100).…”

“…Purified by column chromatography (petroleum ether/EtOAc, 10:1) as a white solid (57.5 mg, 73%); mp 143–145 °C (lit . mp 144–146 °C); IR (KBr) ν 1662 (CO) cm –1 ; 1 H NMR (CDCl 3 , 400 MHz) δ 8.04–7.99 (m, 2H), 7.94–7.91 (m, 2H), 7.51–7.48 (m, 2H), 7.22–7.19 (m, 2H); 13 C­{ 1 H} (100 MHz, CDCl 3 ) δ 192.5, 192.0, 166.9 (d, J = 257.0 Hz), 141.8, 132.8 (d, J = 10.0 Hz), 131.2 (d, J = 2.0 Hz), 129.5, 129.34, 129.31, 116.5 (d, J = 22.0 Hz); MS (EI, 70 eV) m / z (%) 262 (4) [M + ], 123 (100).…”

Synthesis of α‐Aryl Carbonyls via Photoinduced Formation of C−C Bonds

“…α‐Aryl carbonyls are key‐compounds in organic chemistry since are often exploited to build privileged scaffolds of diverse heterocycles, including indoles, [1] oxazoles, [2] pyrazoles [3] and diazepine cores [4] . The common pathway to achieve such structures is by arylation of carbonyls nowadays recognized as the elective key‐strategy for constructing C(sp 2 )−C(sp 3 ) bonds and has been widely used to have access to natural products, pharmaceuticals and biomacromolecules [5–8] .…”