The reaction of 5 (het)aryl 2,3 dicyano 1 ethylpyrazinium salts with phenol derivatives affords relatively stable dihydropyrazines, whereas the reactions of 6 (het)aryl 1,2,5 oxadiazo lo[3,4 b]pyrazin 4 ium protic salts, depending on the phenol structure, result in products of nucleophilic substitution of hydrogen or open chain transformation products: benzo[b]furan substituted derivatives. The crystallographic data on the spatial structure of all types of the synthesized products were obtained. Key words: pyrazinium salts, phenols, 1,2 dihydropyrazines, σ Н adducts, nucleophilic sub stitution of hydrogen (S N H ). as a dark yellow crystalline powder. The yield was 68%, m.p. 166-168 °С. 1 Н NMR (DMSO d 6 ), δ: 7.86 (dd, 1 Н, H(5″) 3 thienyl, J = 5.2 Hz, J = 2.8 Hz); 8.01 (dd, 1 Н, H(4″) 3 thienyl, J = 5.2 Hz, J = 1.2 Hz); 9.05, 7.81 (both dd, 1 Н, H(2″) 3 thienyl, J = 2.8 Hz, J = 1.2 Hz); 9.76 (s, 1 H, С6(H)). Found (%): C, 47.15; Н, 2.03; N, 27.64. С 8 Н 4 N 4 ОS. Calculated (%): C, 47.05; Н, 1.97; N, 27.44.Synthesis of 6 substituted 5 (het)aryl 1 ethyl 1,6 dihydro pyrazine 2,3 dicarbonitriles 11a,b-15a,b (general procedure). A solution of salt 5а or 5b (1.2 mmol) and phenol derivative 6 or 7-10 (1 mmol) in anhydrous MeCN (5-7 mL) was stirred for 1 h at room temperature, the solvent was distilled in vacuo, and the residue was chromatographed eluting with an ethyl ace tate-hexane (1 : 1) mixture. If necessary, the obtained product was additionally recrystallized from an EtOH-H 2 O (1 : 1) mixture.6 (2,4 Dihydroxyphenyl) 1 ethyl 5 phenyl 1,6 dihydropyr azine 2,3 dicarbonitrile (11a). Product 11a was obtained as an orange crystalline powder. The yield was 95%, m.p. 198-201 °С (decomp.). 7.86-7.88 (m, 2 Н, Ph). Found (%): C, 67.57; Н, 4.99; N, 15.61. С 20 Н 16 N 4 O 2 •0.67 H 2 O. Calculated (%): C, 67.42; Н, 4.89; N, 15.73. 6 (2,4 Dihydroxyphenyl) 1 ethyl 5 (3 thienyl) 1,6 dihydro pyrazine 2,3 dicarbonitrile (11b) was obtained as a yellow crys talline powder. The yield was 95%, m.p. 180-182 °С (decomp.). 1 Н NMR (CD 3 CN), δ: 1.19 (t, 3 Н, СН 3 , J = 7.2); 3.53 (dq, 1 Н, NCH A , J = 14.4 Hz, J = 7.2 Hz); 3.59 (dq, 1 Н, NCH B , J = 14.4 Hz, J = 7.2 Hz); 6.07 (s, 1 Н, C(6)Н); 6.30 (dd, 1 Н, С arom (Н(5´)), J = 8.5 Hz, J = 2.4 Hz); 6.38 (d, 1 Н, С arom (Н(3´)), J = 2.4 Hz); 6.91 (d, 1 Н, С arom (Н(6´)), J = 8.5 Hz); 7.12 (s, 1 Н, ОН); 7.27 (dd, 1 Н, H(5″) 3 thienyl, J = 5.2 Hz, J = 2.8 Hz); 7.58 (dd, 1 Н, H(4″) 3 thienyl, J = 5.2 Hz, J = 1.3 Hz); 7.71 (s, 1 Н, ОН); 7.87 (dd, 1 Н, H(2″) 3 thienyl, J = 2.8 Hz, J = 1.3 Hz). Found (%): C, 61.36; Н, 4.06; N, 15.79. С 18 Н 14 N 4 О 2 S. Calculated (%): C, 61.70; Н, 4.03; N, 15.99.6 (2,3,4 Dihydroxyphenyl) 1 ethyl 5 phenyl 1,6 dihydro pyrazine 2,3 dicarbonitrile (12a) was obtained as a yellow crys talline powder. The yield was 60%, m.p. 205-207 °С (decomp.). 1 Н NMR (CD 3 CN), δ: 1.21 (t, 3 Н, СН 3 , J = 7.2 Hz); 3.59 (dq, 1 Н, NCH A , J = 14.4 Hz, J = 7.2 Hz); 3.72 (dq, 1 Н, NCH B , J = 14.4 Hz, J = 7.2 Hz); 6.20 (s, 1 Н, C(6)Н); 6.35 (d, 1 Н, С arom (Н(6´)), J = 8.5 Hz); 6...
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