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Synlett 2014; 25(12): 1759-1763
DOI: 10.1055/s-0033-1338644
DOI: 10.1055/s-0033-1338644
letter
Regioselective One-Pot Synthesis of Isochromenopyrroles Containing a Disulfide Bond
Further Information
Publication History
Received: 22 March 2014
Accepted after revision: 21 April 2014
Publication Date:
28 May 2014 (online)
Abstract
Isochromenopyrroles containing a disulfide bond were prepared by reacting enamines, resulting from propylamine and β-keto esters, with aryl isothiocyanates to give rise to an intermediate which is trapped by ninhydrin. The simple procedure, metal-catalyst-free and mild reaction conditions, good to excellent yields, and no column chromatography are important features of this protocol.
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- 30 A mixture of β-keto ester 1 (1 mmol) and propylamine (1 mmol) was stirred at r.t. for 1 h, after which time a solution of aryl isothiocyanate 2 (1 mmol) in EtOH (2 mL) was added. The mixture was stirred for a further 6 h. Subsequently ninhydrin (1 mmol) was added. Upon completion (1 h), as monitored by TLC, the mixture was filtered and the precipitate was washed with EtOH (4 mL) to afford the pure products 3a–k. Diethyl 2,2′-Disulfanediylbis(5-oxo-3-phenyl-3,5-di-hydroisochromeno[3,4-b]pyrrole-1-carboxylate) (3b): yellow powder; yield: 0.60 g (82%); mp 246–247 °C. IR (KBr): 3060 (CH), 1745 (CO2Et), 1702 (CO2), 1607, 1509 (Ar), 1266, 1181(C–O) cm–1. 1H NMR (300 MHz, DMSO-d 6): δ = 1.16 (br s, 6 H, 2 × Me), 4.14 (d, 3 J HH = 5.0 Hz, 4 H, 2 × OCH2), 6.90–7.23 (m, 4 H, 4 × CH ortho of Ph), 7.25–7.43 (m, 4 H, 4 × CH meta of Ph), 7.48 (t, 3 J HH = 7.0 Hz, 2 H, 2 × CH para of Ph), 7.57 (t, 3 J HH = 7.6 Hz, 2 H, 2 × CH of Ar), 7.92 (t, 3 J HH = 7.5 Hz, 2 H, 2 × CH of Ar), 8.25 (d, 3 J HH = 7.8 Hz, 2 H, 2 × CH of Ar), 8.32 (d, 3 J HH = 8.0 Hz, 2 H, 2 × CH of Ar). 13C NMR (75 MHz, DMSO-d 6): δ = 13.8 (2 × Me), 61.2 (2 × OCH2), 99.4 (2 × C–CO2Et), 117.7 (2 × CH of Ar), 117.8 (2 × C–C ipso ), 121.8 (2 × C ipso of Ar), 123.8 (2 × NCS), 127.1 (2 × CH of Ar), 128.4 (2 × C ipso –CO2), 128.8 (4 × CH ortho of Ph), 129.4 (2 × CH para of Ph), 131.0 (4 × CH meta of Ph), 132.3 (2 × OCN), 133.2 (2 × CH of Ar), 136.0 (2 × CH of Ar), 143.2 (2 × C ipso –N), 159.2 (2 × CO2), 163.5 (2 × CO2Et). MS (EI, 70 eV): m/z = 409, 393, 364, 319, 203, 118, 105, 77. Anal. Calcd for C40H28N2O8S2: C, 65.92; H, 3.87; N, 3.84. Found: C, 65.98; H, 3.91; N, 3.78. Crystal Data for 3b: C40H28N2O9S2 (CCDC 971338): MW = 746.78, monoclinic, space group P21/n, a = 17.084(5) Å, b = 11.082(5) Å, c = 38.698(5) Å, α = 90.00°, β = 100.171(5)°, γ = 90.00°, V = 7211(4) Å3, Z = 8, Dc = 1.376 mg/m3, F (000) = 3104, crystal dimension 0.38 × 0.20 × 0.15 mm, radiation, Mo–Kα (λ = 0.71073 Å), 2.92≤ 2θ≤ 25.05, intensity data were collected at 293(2) K with a Bruker APEX-II CCD area-detector diffractometer, and employing ω/2θ scanning technique, in the range of –20≤ h≤ 17, –10≤ k≤ 13, –41≤ l≤ 46; the structure was solved by a direct method, all non-hydrogen atoms were positioned and anisotropic thermal parameters refined from 7790 observed reflections with R (into) = 0.1201 by a full-matrix least-squares technique converged to R = 0.0766 unrefined = 0.2188 [I >2σ (I)].
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