Tandem Synthesis of Bicyclic ortho‐Aminocarbonitrile Derivatives in Ionic Liquids

Abstract

An efficient synthesis of 2‐amino‐4a,5,6,7‐tetrahydronaphthalene‐1,3,3(4H)‐tricarbonitriles via the tandem four‐component condensation of one equivalent of aromatic aldehyde, cyclohexanone, and two equivalents of malononitrile in ionic liquids was undertaken. Up to four new bonds and one new ring were formed in one‐pot with water as the only by‐product in this multi‐component procedure.

Sonochemical synthesis of ortho‐aminocarbonitrile tetrahydronaphthalenes using mesoporous yolk–shell nanocomposites as a recyclable heterogeneous catalyst and evaluation of their in vitro antimicrobial activities

“…: 282–284°C, (m.p. : 271–272°C) Lit., 30 IR (KBr, ν, cm −1 ): 3445, 3355, 2945, 2853, 2216, 1624, 1441, 1390, 1272, 1041, 749, 510; 1 H NMR (400 MHz, DMSO‐d 6 ) (δ, ppm): 7.79 (dd, J = 8.0 Hz, 1H), 7.62 (d, J = 8.0 Hz, 1H), 7.48–7.58 (m, 2H), 7.45 (s, 2H), 5.77 (s, 1H), 3.88 (d, J = 12.0 Hz, 1H), 2.80–2.92 (m, 1H), 2.02–2.24 (m, 2H), 1.62–1.70 (m, 1H), 1.33–1.50 (m, 2H), 0.75–0.89 (m, 1H).…”

“…: 233–235°C (m.p. : 234–236°C) Lit., 30 IR (KBr, ν, cm −1 ): 3438, 3355, 3246, 2938, 2838, 2203, 1640, 1593, 1509, 1462, 1334, 1246, 1127, 1007, 846, 757, 695; 1 H NMR (400 MHz, DMSO‐d 6 ) (δ, ppm): 7.38 (s, 2H), 6.87 (s, 1H), 6.83 (s, 1H), 5.73 (s, 1H), 3.80 (s, 3H), 3.76 (s, 3H), 3.71 (s, 3H), 3.48 (s, 2H), 2.82 (s, 1H), 2.15–2.27 (m, 2H), 1.64–1.78 (m, 1H), 1.45–1.61 (m, 2H), 0.83–0.97 (m, 1H).…”

“…The precipitate was finally recrystallized from dry ethanol for 24 h at 80°C in order to purify the final product. The resulting products were characterized by melting points and spectroscopic data such as FT‐IR and 1 H NMR and compared with genuine samples 29–33 . The relevant data are reported as follows and also presented in the Supporting Information.…”

“…The resulting products were characterized by melting points and spectroscopic data such as FT-IR and 1 H NMR and compared with genuine samples. [29][30][31][32][33] The relevant data are reported as follows and also presented in the Supporting Information. 34 Rifampin was used as positive control for bacteria.…”

Synthesis of 1H‐isochromenes, 4H‐chromenes, and ortho‐aminocarbonitrile tetrahydronaphthalenes from the same reactants by using metal‐free catalyst

“…Some of these products were tetrahydronaphthalene, 1 H ‐isochromene, and 4 H ‐chromene. Ortho‐aminocarbonitrile tetrahydronaphthalene is useful as a precursor and significant for its optical properties . The various derivatives of 1 H ‐isochromene are present in a diversity of natural products, pharmaceuticals, and bioactive molecules .…”