2-Substituted Amino- and Aminomethyl-4-phenyl-1-tetralones

Synthesis of phenyl-substituted 1-aminotetralines

“…The residue (51 g) was distilled and the fraction (21 g, 58%) boiling at 180-182°(0.15 mm) was collected. A 15-g (0.0415 mol) portion of this fraction was saponified with 37.5 g of 87% KOH, 150 ml of EtOH, and 37.5 ml of H20 at reflux temperature for 3 hr to give, after a crystallization of the acidic product from hexane, 8.6 g (68%) of 43 (R -H): mp 99-100°; NMR (CDCls) 2.5-3.0 (m, 4 ), 3.1-3.7 (m, 1 H), 3.7 (s, 3 H), 6.67 (d, 1 H, J = 9 Hz), 6.95 (d of d, J = 3, 9 Hz), 7.2 (br s, 6 H), 11.5 (br s, 1 H). Anal.…”

“…The reaction of , '-dithiodiisobutyraldehyde (1) with primary aromatic or aliphatic amines afforded novel Schiff bases (2)(3)(4)(5)(6)(7)(8). The reduction of these Schiff bases with sodium borohydride furnished a novel synthesis of 1,1-dimethyl 2-substituted aminoethanethiols (9)(10)(11)(12)(13)(14)(15). Two of the aminoethanethiols (13 and 14) were further characterized by the reaction with carbon disulfide to give the corresponding 3-substituted 5,5-dimethyl-2-thiazolidinethione (16 and 17).…”

“…The reaction of 1 with primary aromatic or aliphatic amines in refluxing heptane containing a catalytic amount of p-toluenesulfonic acid or in methyl alcohol at 25-30°g ave the Schiff bases 2-8 in yields of 82-99%. Reduction of these products with sodium borohydride in refluxing ethanol furnished the aminoethanethiols (9)(10)(11)(12)(13)(14)(15) in good yields. The structures of the Schiff bases and aminoethanethiols were…”

Tandem Oxidative Ring-Opening/Cyclization Reaction in Seconds in Open Atmosphere for the Synthesis of 1-Tetralones in Water–Acetonitrile

“…Tetralone is also commonly used as an organic building block in the synthesis of complex compounds . However, the development of synthetic strategies to achieve 1-tetralones is still in an early stage . The most conventional method for synthesizing 1-tetralones is the Haworth reaction .…”

Novel synthesis of aminoethanethiols

“…An exothermic reaction set in, causing a temperature rise of approximately 10". The crude product was distilled and a 60% yield of 8, bp 86-87" (0.15 mm), nZ6D 1.5220, was obtained NMR (CDCl3) 6 1.3 [s, 12, 2-SC(CH3)2], 3.2 (8, 6, 2-NCHs), 7.4 (9, 1,l-Dimethyl 2-Substituted Aminoethanethiols (9)(10)(11)(12)(13)(14)(15). The solids were collected by filtration and air dried at 25-30'.…”