Synlett 2018; 29(05): 635-639
DOI: 10.1055/s-0036-1591855
letter
© Georg Thieme Verlag Stuttgart · New York

A Convenient Synthesis of Fused Tetrahydroazocines from Acenaphthylene-1,2-dione, Proline, and Acetylenic Esters

Issa Yavari*
a  Department of Chemistry, Tarbiat Modares University, PO Box 14115-175, Tehran, Iran   Email: yavarisa@modares.ac.ir
,
Leila Baoosi
a  Department of Chemistry, Tarbiat Modares University, PO Box 14115-175, Tehran, Iran   Email: yavarisa@modares.ac.ir
,
Mohammad Reza Halvagar
b  Department of Inorganic Chemistry, Chemistry and Chemical Engineering Research Center of Iran, PO Box 14335-186, Tehran, Iran
› Author Affiliations
Further Information

Publication History

Received: 12 August 2017

Accepted after revision: 08 November 2017

Publication Date:
11 December 2017 (eFirst)

Abstract

A synthesis of dialkyl (12E,14E)-7-oxo-10,11-dihydro-7H,9H-azocino[2,1-a]benzo[de]isoquinoline-13,14-dicarboxylates through a 1,3-dipolar cycloaddition reaction of azomethine ylides, generated in situ from proline and acenaphthylene-1,2-dione, with dialkyl acetylenedicarboxylates is described. According to the X-ray diffraction data, the tetrahydroazocine ring has a rigid twist-boat form with approximate local C2 symmetry.

Supporting Information

 
  • References and Notes

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  • 16 Tetrahydroazocines 4; General Procedure A mixture of 1 (1.0 mmol), 2 (1.0 mmol), and 3 (1.0 mmol) in MeOH (15 mL) was refluxed for 24 h. When the reaction was complete (TLC), unreacted starting materials were removed by filtration. The filtrate was evaporated in vacuo, and the residue was crystallized from 80% aq MeOH to afford the products as orange crystals.
  • 17 Diethyl (12E,14E)-7-Oxo-10,11-dihydro-7H,9H-azocino[2,1-a]benzo[de]isoquinoline-13,14-dicarboxylate (4b) Orange crystals; yield: 0.34 g (83%); mp 220–221 °C. IR (KBr): 3539, 2915, 1735, 1649, 1338, 773 cm–1. 1H NMR (300 MHz, CDCl3): δH = 0.90 (t, 3 J = 7.1 Hz, 3 H, Me), 1.29 (t, 3 J = 7.1 Hz, 3 H, Me), 1.31–1.39 (m, 1 H, CH), 1.95–1.98 (m, 1 H, CH), 2.61–2.64 (m, 2 H, CH2), 3.84–4.03 (m, 2 H, CH2O), 3.84–4.04 (m, 1 H, CH–N), 4.24 (q, 3 J = 7.1 Hz, 2 H, CH2O), 5.02–5.06 (m, 1 H, CH–N), 6.86 (t, 3 J = 8.5 Hz, 1 H, CH), 7.46 (t, 3 J = 7.9 Hz, 1 H, CH), 7.67 (t, 3 J = 7.4 Hz, 1 H, CH), 7.88 (d, 3 J = 7.9 Hz, 1 H, CH), 7.97 (d, 3 J = 7.4 Hz, 1 H, CH), 8.06 (d, 3 J = 7.9 Hz, 1 H, CH), 8.41 (d, 3 J = 7.4 Hz, 1 H, CH). 13C NMR (75 MHz, CDCl3): δC = 13.7 (Me), 14.3 (Me), 25.3 (CH2), 39.5 (CH2N), 61.4 (MeO), 61.5 (MeO), 109.6 (CH), 123.6 (CH), 125.9 (C), 126.8 (CH), 127.0 (C), 128.5 (C), 128.8 (C), 130.6 (C), 131.1 (C), 131.7 (CH), 132.4 (C), 137.2 (CH), 139.8 (CH), 146.4 (CH), 162.3 (C=O), 166.9 (C=O), 172.2 (C=O). MS (EI, 70 eV): m/z (%) = 405 (15) [M+], 333 (12), 260 (10), 251 (15), 154 (25), 126 (10), 75 (5). Anal. Calcd for C24H23NO5 (405.45): C, 71.10; H, 5.72; N, 3.45. Found: C, 71.45; H, 5.75; N, 3.48.
  • 18 X-Ray Crystal-Structure Determination of 4b The X-ray diffraction measurements were carried out on STOE IPDS-2T diffractometers with graphite-monochromated Mo(Kα) radiation. All single crystals were mounted on a glass fiber and used for data collection. Orange-colored single crystals of compound 4b, suitable for X-ray analysis were grown by slow evaporation of an aqueous methanol solution. The compound crystallized as a monoclinic crystal system, space group P21/c. Diffraction data were collected in a series of ω scans with 1° oscillations, and integrated by using the STOE X-AREA software package (see Ref. 26). Multiscan absorption corrections were applied by using WinGX-2013.3 software. The structures were solved by direct methods and subsequent difference Fourier maps, and then refined on F2 by a full-matrix least-squares procedure using anisotropic displacement parameters. Atomic factors are from the International Tables for X-ray Crystallography (International Union of Crystallography: Cambridge, UK). All nonhydrogen atoms were refined with aniso­tropic displacement parameters. Hydrogen atoms were placed in ideal positions and refined as riding atoms with relative isotropic displacement parameters. All refinements were performed by using the X-STEP32, SHELXL-2014, and WinGX-2013.3 programs (see ref. 27).
  • 19 CCDC 1507121 contains the supplementary crystallographic data for compound 4b. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
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  • 24 Dimethyl 2-Oxo-1′,7a′-dihydro-2H-spiro[acenaphthylene-1,5′-pyrrolo[1,2-c][1,3]thiazole]-6′,7′-dicarboxylate (8a) Yellow powder; Yield: 0.28 g (70%); mp 218–221 °C. IR (KBr): 3430, 2925, 1730, 1659, 1438, 773 cm–1. 1H NMR (500 MHz, CDCl3): δH = 3.30 (s, 3 H, Me), 3.31–3.38 (m, 2 H, CH2–S), 3.45–3.47 (d, 3 J = 10.8 Hz, 1 H, S–CH–N), 3.87 (s, 3 H, Me), 3.91 (d, 3 J = 10.8 Hz, 1 H, S–CH–N), 5.09 (dd, 3 J = 5.1 Hz, 1 H, CH–N), 7.68 (t, 3 J = 7.5 Hz, 1 H, CH), 7.76 (d, 3 J = 7.0 Hz, 1 H, CH), 7.78 (t, 3 J = 7.0 Hz, 1 H, CH), 7.96 (d, 3 J = 7.5 Hz, 1 H, CH), 8.05 (d, 3 J = 7.0 Hz, 1 H, CH), 8.15 (d, 3 J = 7.5 Hz, 1 H, CH). 13C NMR (125 MHz, CDCl3): δC = 32.5 (CH2), 46.9 (MeO), 47.4 (MeO), 50.0 (CH2), 70.3 (CH), 77.7 (C), 117.6 (CH), 119.1 (CH), 121.3 (C), 123.1 (CH), 123.3 (CH), 125.6 (C), 126.0 (C), 126.6 (CH), 127.0 (C), 132.8 (C), 135.1 (C), 137.5 (C), 156.7 (C=O), 158.1 (C=O), 193.6 (C=O). MS (EI, 70 eV): m/z (%) = 395 (20) [M+], 336 (10), 277 (15), 253 (20), 241 (30), 75 (5). Anal. Calcd for C21H17NO5S (395.43): C, 63.79; H, 4.33; N, 3.54. Found: C, 63.45; H, 4.32; N, 3.57.
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