A Synthesis of Novel Dioxapropellanes from the Knoevenagel Adducts of Acenaphthoquinone and 3-Oxo-3-arylpropionitriles in Aqueous Methanol

Issa Yavari; Aliyeh Khajeh-Khezri; Samira Bahemmat; Mohammad Reza Halvagar

doi:10.1055/s-0036-1588822

Synlett, Inhaltsverzeichnis

Synlett 2017; 28(14): 1785-1788
DOI: 10.1055/s-0036-1588822

letter

A Synthesis of Novel Dioxapropellanes from the Knoevenagel Adducts of Acenaphthoquinone and 3-Oxo-3-arylpropionitriles in Aqueous Methanol

Authors

Issa Yavari*

^aDepartment of Chemistry, Tarbiat Modares University, PO Box 14115-175, Tehran, Iran eMail: yavarisa@modares.ac.ir
Aliyeh Khajeh-Khezri

^aDepartment of Chemistry, Tarbiat Modares University, PO Box 14115-175, Tehran, Iran eMail: yavarisa@modares.ac.ir
Samira Bahemmat

^bDepartment of Inorganic Chemistry, Chemistry and Chemical Engineering Research Center of Iran, PO Box 14335-186 Tehran, Iran
Mohammad Reza Halvagar

^bDepartment of Inorganic Chemistry, Chemistry and Chemical Engineering Research Center of Iran, PO Box 14335-186 Tehran, Iran

Abstract

Alle Artikel dieser Rubrik

Abstract

A highly chemoselective and regioselective method for the synthesis of dioxopropellanes developed by reaction of the Knoevenagel adducts of acenaphthoquinone (and ninhydrin) and malononitrile, with 3-oxo-3-arylpropionitriles in 70% aqueous MeOH at room temperature, is reported.

Key words

dioxapropellane - acenaphthoquinone - chemoselective - regioselective

Volltext

Referenzen

References and Notes
1 Ginsburg D. Propellanes: Structure and Reactions . Verlag Chemie; Weinheim: 1975

For reviews, see:

2a Diels O. Alder K. Justus Liebigs Ann. Chem. 1931; 486: 191
2b Diels O. Friedrichsen W. Justus Liebigs Ann. Chem. 1934; 513: 145
2c Fieser LF. Dunn JT. J. Am. Chem. Soc. 1936; 58: 1054
2d Alder K. Backendorf KH. Chem. Ber. 1938; 71: 2199
2e Brigl P. Herrmann R. Chem. Ber. 1938; 71: 2280

3a Snatzke G. Zanati G. Justus Liebigs Ann. Chem. 1965; 684: 62
3b Altman J. Babad E. Itzchaki J. Ginsburg D. Tetrahedron 1966; 22: 279

4 Nerdel F. Janowsky K. Frack D. Tetrahedron Lett. 1965; 2979

5a Levin MD. Kaszynski P. Michel J. Chem. Rev. 2000; 100: 169
5b Ainoliisa JP. Ari MP. K. Tetrahedron 2005; 61: 8769

6a Navarro R. Reisman SE. Org. Lett. 2012; 14: 4354
6b Dyker G. Körning J. Bubenitschek P. Jones PG. J. Chem. Res., Synop. 1997; 132
6c Wiberg KB. Chem. Rev. 1989; 89: 975

7a Sugimoto Y. Babiker HA. A. Saisho T. Furumoto T. Inanaga S. Kato M. J. Org. Chem. 2001; 66: 3299
7b Miao M. Cao J. Zhang J. Huang X. Wu L. J. Org. Chem. 2013; 78: 2687
7c Dave PR. Duddu R. Yang K. Damavarapu R. Gelber N. Surapaneni R. Gilardi R. Tetrahedron Lett. 2004; 45: 2159
7d Pihko AJ. Koskinen AM. P. Tetrahedron 2005; 61: 8769
7e Qian-Cutrone J. Gao Q. Huang S. Klohr SE. Veitch JA. Shu YZ. J. Nat. Prod. 1994; 57: 1656
7f Zhang LJ. Yan CG. Tetrahedron 2013; 69: 4915
7g Jansone-Popova S. May JA. J. Am. Chem. Soc. 2012; 134: 17877

8 Nicolaou KC. Snyder SA. Montagnon T. Vassilikogiannakis G. Angew. Chem. Int. Ed. 2002; 41: 1668
9 Navarro R. Reisman SE. Org. Lett. 2012; 14: 4354
10 Trost BM. Shi Y. J. Am. Chem. Soc. 1991; 113: 701
11 Asahi K. Nishino H. Tetrahedron 2008; 64: 1620
12 Fitjer L. Kanschik A. Majewski M. Tetrahedron 1994; 50: 10867
13 Jamrozik J. Jamrozik M. Sciborowicz P. Zeslawski W. Monatsh. Chem. 1995; 126: 587
14 Yang D. Fu L. Shi D. Li J. Zhang QJ. Chem. Eng. Data 2016; 61: 3277

15a Yamamoto N. Fujii H. Nemoto T. Nakajima R. Momen S. Izumimoto N. Hasebe K. Mochizuki H. Nagase H. Bioorg. Med. Chem. Lett. 2011; 21: 4104
15b Nagase H. Akiyama J. Nakajima R. Hirayama S. Nemoto T. Gouda H. Hirono S. Fujii H. Bioorg. Med. Chem. Lett. 2012; 22: 2775
15c Fujii H. Nakajima R. Akiyama J. Yamamoto N. Hirayama S. Nemoto T. Gouda H. Hirono S. Nagase H. Bioorg. Med. Chem. Lett. 2012; 22: 7697
15d Rezvanian A. Alizadeh A. Zhu LG. Synlett 2012; 23: 2526
15e Alizadeh A. Bayat F. Sadeghi V. Lett. Org. Chem. 2015; 12: 153
15f Zhang LJ. Yan CG. Tetrahedron 2013; 69: 4915

16 Yavari I. Malekafzali A. Skoulika S. Tetrahedron Lett. 2014; 55: 3154

17a Chen NY. Ren LP. Zou MM. Xu ZP. Shao XS. Xu XY. Li Z. Chin. Chem. Lett. 2014; 25: 197
17b Mhaidat I. Hamilakis S. Kollia C. Tsolomitis A. Loizos Z. Mat. Lett. 2007; 61: 321

18 Joubran L. Jackson WR. Campi EM. Robinson AJ. Wells BA. Godfrey PD. Callaway JK. Jarrott B. Aust. J. Chem. 2003; 56: 597
19 Typical Procedure for the Preparation of 3a–f To a stirred solution of 3-oxo-3-arylpropionitrile 2 and Et₃N (0.101 g, 1 mmol) in MeOH–H₂O (2:1, 6 mL) was added the adduct of acenaphthoquinone and malononitrile or ethyl cyanoacetate 1 (1 mmol) at r.t. After completion of the reaction (about 30–120 min, TLC (n-hexane–EtOAc, 2:1) monitoring), the solvent was evaporated under vacuum, and the crude product was purified by flash column chromatography on silica gel using EtOAc–n-hexane (1:2) as eluent (for compounds 3a–d) and was washed with MeOH (for compounds 3e–h) to afford the pure product.
20 Ethyl 8-Amino-10-cyano-11-phenyl-6b,9a-(epoxyetheno)-acenaphtho[1,2-b]furan-9-carboxylate (3e) Colorless solid; yield 0.40 g (95%), mp 213–216 °C. ¹H NMR (500.1 MHz, DMSO-d ₆): δ = 1.42 (3 H, br, CH₃), 4.25 (2 H, br, OCH₂), 7.48–7.50 (4 H, m, 4 Ar–H), 7.68–7.73 (3 H, m, 3 ArH), 7.82–7.92 (5 H, m, 3 ArH, NH₂), 8.02 (1 H, d, ³ J = 7.4 Hz, ArH). ¹³C NMR (125.7 MHz, DMSO-d ₆): δ = 14.4 (Me), 58.7 (CCN), 59.8 (OCH₂) 70.8(C), 77.7 (CCN), 90.1 (OCO), 116.0 (CN), 120.4 (CH), 120.8 (CH), 124.5 (CH), 125.6 (C), 126.4 (CH), 126.8 (2 CH), 127.6 (2 CH), 129.0 (2 CH), 129.1 (CH), 131.5 (C), 134.8 (C), 135.8 (C), 141.2 (C), 165.0 (CO₂Et), 165.2 (CNH₂), 165.9 (CO). IR (KBr): ν_max = 3397 and 3294 (NH₂), 2208 (CN), 1688 (C=O), 1628 (OC=C), 1540, 1430 (C=C_Ar) cm^–1. MS (EI): m/z (%) = 422 (10) [M⁺], 366 (25), 343 (45), 264 (50), 236 (30), 210 (25), 183 (17), 149 (60), 105 (100), 77 (90), 51 (40). Anal. Calcd (%) for C₂₆H₁₈N₂O₄ (422.13): C, 73.92; H, 4.30; N, 6.63. Found: C, 74.12; H, 4.40; N, 6.72. X-ray Crystal-Structure Determination of 3e The X-ray diffraction measurement was carried out on a STOE IPDS 2T diffractometer with graphite-monochromated Mo Kα radiation. The single crystal suitable for X-ray analysis was obtained from DMSO solution and mounted on a glass fiber. Compound 3e crystallized in the triclinic system with the P-1 space group. For the unit cell a = 9.167(18) Å, b = 11.425(2) Å, c = 11.630(2) Å, α = 69.01(3)°, β = 70.11(3)°, γ = 82.22(3)°, Z = 2, cell volume = 1069.3(4) Å³. Orientation matrixes for data collection were obtained by least-square refinement of the diffraction data from 3053 reflections. Diffraction data were collected in a series of ω scans in 1° oscillations and integrated using the Stoe X-AREA software package.²³ Numerical absorption correction was applied using X-Red32 software. The structure was solved by direct methods and subsequent difference Fourier maps and then refined on F² to final R1 = 0.0591 and wR2 (all data) = 0.1535 by a full-matrix least-squares procedure using anisotropic displacement parameters. Atomic factors are from the International Tables for X-ray crystallography. 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 using the X-STEP32, SHELXL-2014 and WinGX-2013.3 programs.²⁴ CCDC-1525132 contains the supplementary crystallographic data for compound 3e in this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
21 Typical Procedure for the Preparation of Compound 10a–d To a stirred solution of 3-oxo-3-arylpropionitrile 2 and Et₃N (0.101 g, 1 mmol) in MeOH–H₂O (2:1, 6 mL) was added the adduct of ninhydrin and malononitrile 9 (0.208 g, 1 mmol) at r.t. After completion of the reaction (about 30–120 min, TLC (n-hexane–EtOAc, 2:1) monitoring), the solvent was evaporated under vacuum, and the crude product was crystallized from CH₂Cl₂–n-hexane.
22 2-Amino-4-oxo-10-phenyl-4a,5-dihydro-4H-8b,3a-(epoxyetheno)indeno[1,2-b]furan-3,11-dicarbonitrile (10a) Orange solid; yield 0.32 g (91%), mp 205–208 °C. ¹H NMR (500.1 MHz, DMSO-d ₆): δ = 7.57 (2 H, t, ³ J = 8.5 Hz, 2 ArH), 7.62 (1 H, t,³ J = 8.0 Hz, ArH), 7.85–7.88 (3 H, m, 3 ArH), 7.99 (1 H, d, ³ J = 7.5 Hz, ArH), 8.04 (1 H, t, ³ J = 7.5 Hz, ArH), 8.09 (1 H, d, ³ J = 8.0 Hz, ArH), 8.17 (2 H, s, NH₂). ¹³C NMR (75.0 MHz, DMSO-d ₆): δ = 52.3 (CCN), 55.9 (C), 69.3 (CCN), 85.3 (OCO), 115.3, 116.8 (2 CN), 120.4 (C), 125.8 (CH), 126.5 (CH), 126.8 (C), 128.2 (2 CH), 130.3 (CH), 134.0 (CH), 134.2 (CH), 136.2 (CH), 138.8 (CH), 143.5 (C), 167.1 (CO), 167.6 (CNH₂), 202.1 (C=O). IR (KBr): ν_max = 3447 and 3335 (NH₂), 2202 (CN), 1725 (C=O), 1662 (OC=C), 1600, 1430 (C=C_Ar) cm^–1. MS (EI): m/z (%) = 353 (25) [M⁺], 341 (65), 249 (32), 205 (47), 149 (33), 105 (100), 77 (82), 51 (70). Anal. Calcd (%) for C₂₁H₁₁N₃O₃ (353.08): C, 71.39; H, 3.14; N, 11.89. Found: C, 71.62; H, 3.28; N, 11.97.
23 X-AREA: Program for the Acquisition and Analysis of Data, Version 1.30. Stoe & Cie GmbH; Darmstadt: 2005

For details, see:

24a Farrugia LJ. J. Appl. Crystallogr. 1999; 32: 837
24b Allen FH. Johnson O. Shields GP. Smith BR. Towler M. J. Appl. Crystallogr. 2004; 37: 335
24c Macrae CF. Edgington PR. McCabe P. Pidcock E. Shields GP. Taylor R. Towler M. van der Streek J. J. Appl. Crystallogr. 2006; 39: 453
24d Burnett MN. Johnson CK. ORTEP-III Report ORNL-6895 . Oak Ridge National Laboratory; Tennessee: 1996
24e Spek AL. J. Appl. Crystallogr. 2003; 36: 7
24f Sheldrick GM. Acta Crystallogr., Sect. A 2008; 64: 112
24g Coppens P. Leiserowitz L. Rabinovich D. Acta Crystallogr. 1965; 18: 1035

Zusatzmaterial

Supporting Information (PDF)