Heterocycles Synthesis Based on Arylation Products of Unsaturated Compounds: XII. Reactions of 2-Aryl-1,4-benzoquinones with Dithiol Compounds

Synthesis of heterocycles on the basis of arylation products of unsaturated compounds: XX. Reaction of 2-aryl-1,4-benzoquinones with potassium O-butyl carbonodithioate

“…The mass spectra (electron impact, 70 eV) were obtained on a Finnigan MAT Incos-50 GC-MS system. Initial 2-aryl-1,4-benzoquinones Ia-Ig were synthesized as described in [12,13,[18][19][20].…”

“…Intermediate thiuronium salt thus formed undergoes intramolecular cyclization with formation of 7-aryl-5-hydroxy-1,3-benzoxathiol-2-ones. The reactions of 2-aryl-1,4-benzoquinones with dithiols gave 1,3-benzodithiole or 1,3-benzoxathiole derivatives, depending on the substituent in the aromatic ring [18]. In the present work we examined reactions of 2-aryl-1,4-benzoquinones with potassium O-butyl carbonodithioate.…”

C–H Arylation of Benzoquinone in Water through Aniline Activation: Synergistic Effect of Graphite-Supported Copper Oxide Nanoparticles

“…The crude product was purified by flash chromatography on silica gel to give the product as a brown solid (179.4 mg, 79%): R f = 0.24 (petroleum ether/DCM 60/40); mp 60–63 °C (lit . mp 60–61 °C); 1 H NMR (400 MHz, DMSO- d 6 ) δ 7.87 (s, 1H), 7.84–7.82 (m, 2H), 7.70 (app t, 1H, J = 7.8 Hz), 7.07 (d, 1H, J = 2.5 Hz), 7.02–6.93 (m, 2H); 13 C NMR (100 MHz, DMSO- d 6 ) δ 187.6, 186.1, 143.9, 137.3, 136.1, 133.8, 133.3, 133.1, 129.3, 129.0 (q, J = 31.0 Hz), 126.1, 126.0, 124.0 (q, J = 271.0 Hz); 19 F NMR (376 MHz, DMSO- d 6 ) δ −61.13; IR ν 3052, 1659, 1609, 1586 cm –1 ; HRMS (ESI) calcd for C 13 H 8 F 3 O 2 [M + H] + 253.0482, found 253.0482.…”