2973-17-3, 2973-17-3 1-Allyl-1H-pyrrole-2,5-dione 18098, apyrrolines compound, is more and more widely used in various fields.
2973-17-3, 1-Allyl-1H-pyrrole-2,5-dione is a pyrrolines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated
General procedure: A solution of 2.5 mmol of 3-N-methylcytisine 2 and 12.5 mmol of N-substituted maleimide in 10 ml of toluene was refluxed under AP until the starting reactant disappeared (TLC monitoring). Then the solvent was evaporated in vacuo. The crude product was chromatographed on SiO2 with a mixture of CHCl3 and CH3OH as the eluent to afford a-adduct and b-adduct. (3aS,4R,8S,12S,12aR,12bS)-2-allyl-10-methyloctahydro-1H- 4,12a-etheno-8,12-methanopyrrolo[3?,4′:3,4]pyrido[1,2-a][1,5] diazocine-1,3,5(4H)-trione 19a and 1(3aR,4S,8S,12S,12aS,12bR)-2- allyl-10-methyloctahydro-1H-4,12a-etheno-8,12-methanopyrrolo [3?,4′:3,4]pyrido[1,2-a][1,5]diazocine-1,3,5(4H)-trione 19b. Compounds 19a (0.146 g) and 19b (0.122 g) were obtained from 0.2 g of 2 (1 mmol) and 0.68 g of 8 (5 mmol) in a 80% total yield. 19a: White crystals, m.p. 148-150 C (EtOAc), [a]20D = 11.0 (c 1.6, CHCl3). 13C NMR (CDCl3, d, ppm): 25.55 (C15); 26.76 (C8); 33.69 (C12); 40.99 (C10); 41.62 (C3a); 45.17 (C4); 46.56 (C100); 47.35 (C12b); 47.54 (C7); 58.11 (C11); 62.28 (C9); 63.71 (C12a); 118.58 (C30); 130.06 (C14); 130.27 (C20); 139.83 (C13); 172.56 (C5); 174.91 (C1); 175.40 (C3). 15N NMR (CDCl3, d, ppm): 124.94 (N6); 184.00 (N2). 1H NMR (CDCl3, d, ppm, J Hz): 1.72 (br.s, 2H, H-15); 2.16 (m, 1H, Hb-11); 2.17 (m, 1H, Hb-9); 2.20 (m, 1H, H-8); 2.23 (s, 3H, H-100); 2.49 (m, 1H, H-12); 2.80 (br.d, 1H, 2J = 11.5, Ha-9); 3.32 (dd, 1H, 2J = 13.2, 3J7b-8 = 7.1, Hb-7); 3.34 (dd, 1H, 3J3a-12b = 8.0, 3J3a-4 = 3.4, H-3a); 3.40 (br.d, 1H, 2J = 13.2, Ha-7); 3.67 (br.d, 1H, 2J = 12.3, Ha-11); 3.85 (d, 1H, 3J12b-3a = 8.0, H-12b); 3.89 (ddd, 1H, 3J4-14 = 6.0, 3J4-3a = 3.2, 4J4- 13= 1.4, H-4); 4.00 (dt, 2H, 3J1′-2′ = 6.0, 4J1′-3’A(3’B) = 1.6, H-1?); 5.16 (qd, 1H, 2J = 1.6, 3J3’A 2′ = 10.0, 4J3’A 1′ = 1.6, HA-3?); 5.19 (qd, 1H, 2J = 1.6, 3J3’B 2′ = 17.1, 4J3’B 1′ = 1.6, HB-3?); 5.67 (ddt, 1H, 3J2′-3’B = 17.1, 3J2′-3’A = 10.0, 3J2′-1′ = 6.0, H-2?); 6.22 (dd, 1H, 3J13-14 = 7.5, 4J13-4 = 1.4, H-13); 6.31 (dd, 1H, J14-13 = 7.5, J14-4 = 6.0, H-14).
2973-17-3, 2973-17-3 1-Allyl-1H-pyrrole-2,5-dione 18098, apyrrolines compound, is more and more widely used in various fields.
Reference£º
Article; Tsypysheva, Inna; Koval’skaya, Alena; Petrova, Polina; Lobov, Alexander; Borisevich, Sophia; Tsypyshev, Dmitry; Fedorova, Victoria; Gorbunova, Elisaveta; Galochkina, Anastasia; Zarubaev, Vladimir; Tetrahedron; vol. 75; 21; (2019); p. 2933 – 2943;,
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