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Synlett 2018; 29(07): 885-889
DOI: 10.1055/s-0037-1609201
DOI: 10.1055/s-0037-1609201
letter
Diastereoselective One-Pot Tandem Synthesis of Chromenopyridodiazepinones through 1,4- and 1,6-Aza-Conjugate Additions/Heterocyclizations
Thanks are due to University of Aveiro and FCT/MEC for financial support to the QOPNA research project (FCT UID/QUI/00062/2013), to the CICECO-Aveiro Institute of Materials (POCI-01-0145-FEDER-007679; FCT UID/CTM/50011/2013), financed by national funds, and, when appropriate, co-financed by FEDER under the PT2020 Partnership Agreement, and to the Portuguese NMR Network. We would like also to thank FCT/MEC and the General Directorate for Scientific Research and Technological Development (DGRSDT) of Algeria and Agence Thématique de Recherche en Sciences et Technologie ATRST for approving the co-financed bilateral project PT-DZ/0005. We further wish to thank CICECO for funding the purchase of the single-crystal X-ray diffractometer.
Further Information
Publication History
Received: 19 November 2017
Accepted after revision: 20 December 2017
Publication Date:
30 January 2018 (online)
Abstract
We report an efficient one-pot synthesis of a novel series of chromenopyridodiazepinone polyheterocycles by a catalyst-free nucleophilic addition of ethane-1,2-diamine to (E,E)-3-[3-(2-hydroxyphenyl)-3-oxoprop-1-en-1-yl]-2-styrylchromones at room temperature under mild conditions. The reaction proceeds by a tandem process involving 1,4- and 1,6-aza-conjugate additions of one amino group of ethane-1,2-diamine to the α,β-unsaturated (3-oxoprop-1-en-1-yl) and the α,β,γ,δ-diunsaturated (2-styrylchromone) carbonyl system of the precursor, followed by imine condensation of the remaining amino group to generate the chromenopyridodiazepinone polyheterocycle. All compounds were characterized by means of one- and two-dimensional NMR spectroscopy and single-crystal X-ray crystallography.
Key words
styrylchromones - ethanediamine - chromenopyridodiazepinones - one-pot synthesis - tandem reaction - aza-conjugated additionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609201.
- Supporting Information
- CIF File
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References and Notes
- 1a Gilchrist TA. J. Chem. Soc., Perkin Trans. 1 1998; 615
- 1b Amishiro N. Okamoto A. Murakata C. Tamaoki T. Okabe M. Saito H. J. Med. Chem. 1999; 42: 2946
- 1c Gribble GW. J. Chem. Soc., Perkin Trans. 1 2000; 1045
- 2a Palomo C. Oiarbide M. Landa A. González-Rego MC. García JM. González A. Odriozola JM. Martın-Pastor M. Linden A. J. Am. Chem. Soc. 2002; 124: 8637
- 2b Franke K. Porzel A. Schmidt J. Phytochemistry 2002; 61: 873
- 2c Toshima K. Kimura T. Takano R. Ozawa T. Ariga A. Shima Y. Umezawa K. Matsumura S. Tetrahedron 2003; 59: 7057
- 2d Kamal A. Ramu R. Khanna GB. R. Saxena AK. Shanmugavel M. Pandita RM. ARKIVOC 2005; (iii): 83
- 2e Ohshita K. Ishiyama H. Oyanagi K. Nakata H. Kobayashi J. Bioorg. Med. Chem. 2007; 15: 3235
- 2f Belluti F. Fontana G. Dal Bo L. Carenini N. Giommarelli C. Zunino F. Bioorg. Med. Chem. 2010; 18: 3543
- 2g Romanov VE. Shul’ts EE. Shakirov MM. Tolstikov GA. Dokl. Chem. (Engl. Transl.) 2010; 430: 27
- 2h Belovodskii AV. Shul’ts EE. Shakirov MM. Romanov VE. Elmuradov BZ. Shakhidoyatov KM. Tolstikov GA. Chem. Nat. Compd. 2011; 46: 880
- 3 Talhi O. Fernandes JA. Pinto DC. G. A. Almieda Paz FA. Silva AS. M. Tetrahedron 2013; 69: 5413
- 4 Thurston DE. Bose DS. Chem. Rev. 1994; 94: 433
- 5a Hsu MC. Schutt AD. Holly M. Slice LW. Sherman MI. Richman DD. Potash MJ. Volsky DJ. Science 1991; 254: 1799
- 5b De Clercq E. Antiviral Res. 1998; 38: 153
- 6a Gregson SJ. Howard PW. Corcoran KE. Jenkins TC. Kelland LR. Thurston DE. Bioorg. Med. Chem. Lett. 2001; 11: 2859
- 6b Gregson SJ. Howard PW. Corcoran KE. Barcella S. Yasin MM. Hurst AA. Jenkins TC. Kelland LR. Thurston DE. Bioorg. Med. Chem. Lett. 2000; 10: 1845
- 7a Kornecki E. Ehrlich YH. Lenox RH. Science 1984; 226: 1454
- 7b Fiakpui CY. Phillips OA. Murthy KS. K. Knavs EE. Drug Des. Discovery 1993; 10: 45
- 7c Thurston DE. Bose DS. Howard PW. Jenkins TC. Leoni A. Baraldi PG. Guiotto A. Cacciari B. Kelland LR. Foloppe MP. Rault S. J. Med. Chem. 1999; 42: 1951
- 7d Lisowski V. Fabis F. Pierré A. Caignard DH. Renard P. Rault S. J. Enzym. Inhib. Med. Chem. 2002; 17: 403
- 8a Abrous L. Hynes JJr. Friederich SR. Smith AB. III. Hirschmann R. Org. Lett. 2001; 3: 1089
- 8b Surman MD. Mulvihill MJ. Miller MJ. Org. Lett. 2002; 4: 139
- 8c Herrero S. García-López MT. Herranz R. J. Org. Chem. 2003; 68: 4582
- 8d Beccalli EM. Broggini G. Paladino G. Pilati T. Pontremoli G. Tetrahedron: Asymmetry 2004; 15: 687
- 8e Matthews JM. Dyatkin AB. Evangelisto M. Gauthier DA. Hecker LR. Hoekstra WJ. Liu F. Poulter B. Sorgi KL. Maryanoff BE. Tetrahedron: Asymmetry 2004; 15: 1259
- 8f Hemming K. Loukou C. Tetrahedron 2004; 60: 3349
- 8g De Silva RA. Santra S. Andreana PR. Org. Lett. 2008; 10: 4541
- 8h Shaabani A. Maleki A. Mofakham H. J. Comb. Chem. 2008; 10: 595
- 9a Beccalli EM. Broggini G. Paladino G. Zoni C. Tetrahedron 2005; 61: 61
- 9b Legerén L. Domínguez D. Tetrahedron Lett. 2010; 51: 4053
- 10a Canonne P. Akssira M. Dahdouh A. Kasmi H. Boumzebra M. Heterocycles 1993; 36: 1305
- 10b El Bouakher A. Laborie H. Aadil M. El Hakmaoui A. Lazar S. Akssira M. Viaud-Massuard M.-C. Tetrahedron Lett. 2011; 52: 5077
- 11a Price WA. Silva AM. S. Cavaleiro JA. S. Heterocycles 1993; 36: 2601
- 11b Desideri N. Conti C. Mastromarino P. Mastropaolo F. Antiviral Chem. Chemother. 2000; 11: 373
- 11c Gomes A. Fernandes E. Silva AM. S. Pinto DC. G. A. Cavaleiro JA. S. Lima JL. F. C. Bioorg. Med. Chem. 2007; 15: 6027
- 11d Gomes A. Fernandes E. Garcia MB. Q. Silva AM. S. Pinto DC. G. A. Cavaleiro JA. S. Lima JL. F. C. Bioorg. Med. Chem. 2008; 16: 7939
- 11e Marinho J. Pedro M. Pinto DC. G. A. Silva AM. S. Cavaleiro JA. S. Sunkel CE. São José Nascimento M. Biochem. Pharmacol. 2008; 75: 826
- 11f Gomes A. Fernandes E. Silva AM. S. Pinto DC. G. A. Cavaleiro JA. S. Lima JL. F. C. Biochem. Pharmacol. 2009; 78: 171
- 11g Shaw AY. Chang C.-Y. Liau H.-H. Lu P.-J. Chen H.-L. Yang C.-N. Li H.-Y. Eur. J. Med. Chem. 2009; 44: 2552
- 11h Gomes A. Freitas M. Fernandes E. Lima JL. Mini-Rev. Med. Chem. 2010; 10: 1
- 11i Rocha-Pereira J. Cunha R. Pinto DC. G. A. Silva AM. S. São José Nascimento M. Bioorg. Med. Chem. 2010; 18: 4195
- 11j Yang C.-H. Yang Y. Liu J.-H. Phytochem. Lett. 2013; 6: 387
- 11k Lin C. Lu P.-J. Yang C.-N. Hulme C.-A. Shaw Y. Med. Chem. Res. 2013; 22: 2385
- 11l Pawar SP. Kondhare DD. Zubaidha PK. Med. Chem. Res. 2013; 22: 753
- 11m Ujwala B. Priyadarsini P. Madhavarao V. Int. J. Pharm. Biol. Sci. 2013; 4 (i): 199
- 11n Yadav P. Parshad B. Manchanda P. Sharma SK. Curr. Top. Med. Chem. (Sharjah, United Arab Emirates) 2014; 14: 2552
- 11o Santos CM. M. Silva AM. S. Eur. J. Org. Chem. 2017; 3115
- 12a Silva AM. S. Pinto DC. G. A. Cavaleiro JA. S. Levai A. Patonay T. ARKIVOC 2004; (vii): 106
- 12b Hayashi Y. Okamura D. Umemiya S. Uchimaru T. ChemCatChem 2012; 4: 959
- 12c Talhi O. Brodziak-Jaroz L. Panning J. Orlikova B. Zwergel C. Tzanova T. Philippot S. Pinto DC. G. A. Almeida Paz FA. Gerhäuser C. Dick TP. Jacob C. Diederich M. Bagrel D. Kirsch G. Silva AM. S. Eur. J. Org. Chem. 2016; 965
- 13 Chromenopyridodiazepinones 2a–c; General Procedure Ethane-1,2-diamine (10 mmol) was added to a stirred solution of the appropriate styrylchromone 1a–c 12c (1 mmol) in THF (20 mL), and the mixture was stirred for 2 h at r.t. The solvent was removed under reduced pressure, and the resulting resinous material was subjected to short-plug silica-gel column chromatography. The product was crystallized from 1:1 hexane–CH2Cl2 by slow evaporation at 6 °C to afford bright-yellow crystals. Good-quality single crystals suitable for X-ray analysis were obtained for 2a and 2c only.
- 14 2-(2-Hydroxyphenyl)-7-(4-methoxyphenyl)-1,4,5,7,8,14b-hexahydro-14H-chromeno[3′,2′:3,4]pyrido[1,2-d][1,4]diazepin-14-one (2a) Yellow crystals; yield: 0.34 g (73%); mp 241–242 °C. 1H NMR (300.13 MHz, CDCl3): δ = 2.84–3.13 (m, 4 H, H-4, H-5), 3.30 (dd, J = 15.3, 9.5 Hz, 1 H, H-1), 3.50 (dd, J = 15.0, 4.7 Hz, 1 H, H-8), 3.59 (d, J = 15.3 Hz, 1 H, H-1), 3.84 (s, 3 H, 4′′-OCH 3), 4.00 (dd, J = 15.0, 9.0 Hz, 1 H, H-8), 4.49 (dd, J = 9.0, 4.7 Hz, 1 H, H-7), 4.61 (d, J = 9.5 Hz, 1 H, H-14b), 6.83–6.99 (m, 4 H, H-5′, H-3′, H-3′′,5′′), 7.28–7.37 (m, 3 H, H-4′, H-2′′,6′′), 7.39–7.44 (m, 2 H, H-10, H-12), 7.67 (ddd, J = 8.8, 7.2, 1.7 Hz, 1 H, H-11), 8.08 (dd, J = 8.1, 1.4 Hz, 1 H, H-6′), 8.30 (dd, J = 9.0, 1.7 Hz, 1 H, H-13), 16.43 (br s, 1 H, 2′-OH). 13C NMR (75.47 MHz, CDCl3): δ = 31.0 (C-1), 45.1 (C-8), 37.3 and 50.1 (C-4, C-5), 52.1 (C-14b), 55.3 (4′′-OCH3), 55.9 (C-7), 114.5 (C-3′′,5′′), 117.3 (C-5′), 117.8 (C-10), 118.8 (C-1′, C-3′), 119.7 (C-14a), 123.5 (C-13a), 124.9 (C-12), 126.0 (C-13), 129.49 and 129.52 (C-2′′,6′′, C-6′), 131.4 (C-1′′), 133.1 (C-4′), 133.5 (C-11), 155.8 (C-9a), 159.5 (C-4′′), 162.2 (C-8a), 165.0 (C-2′), 175.6 (C-14), 177.1 (C-2). HRMS-ESI+: m/z [M + H]+ calcd for C29H27N2O4: 467.1971; found: 467.2011.
- 15 7-(3,4-Dimethoxyphenyl)-2-(2-hydroxyphenyl)-1,4,5,7,8,14b-hexahydro-14H-chromeno[3′,2′:3,4]pyrido[1,2-d][1,4]diazepin-14-one (2b) Yellow crystals; yield: 0.26 g (52%); mp 253–254 °C. 1H NMR (300.13 MHz, CDCl3): δ = 2.84–3.18 (m, 4 H, H-4, H-5), 3.32 (dd, J = 15.3, 9.5 Hz, 1 H, H-1), 3.50 (dd, J = 15.0, 4.7 Hz, 1 H, H-8), 3.56 (d, J = 15.3 Hz, 1 H, H-1[M′]), 3.90 and 3.92 (2s, 6 H, 3′′- and 4′′-OCH 3), 4.02 (dd, J = 15.0, 9.0 Hz, 1 H, H-8), 4.49 (dd, J = 9.0, 4.7 Hz, 1 H, H-7), 4.65 (d, J = 9.5 Hz, 1 H, H-14b), 6.84–7.01 (m, 5 H, H-5′, H-3′, H-2′′, H-5′′, H-6′′), 7.28–7.36 (m, 1 H, H-4′), 7.37–7.47 (2 H, H-10, H-12), 7.56–778 (m, 1 H, H-11), 8.07 (d, J = 7.8 Hz, 1 H, H-6′), 8.30 (dd, J = 8.1, 1.4 Hz, 1 H, H-13), 16.38 (br s, 1 H, 2′-OH). 13C NMR (75.47 MHz, CDCl3): δ = 30.9 (C-1), 45.0 (C-8), 37.2 and 50.0 (C-4, C-5), 52.1 (C-14b), 55.89 (C-7), 55.99 and 56.0 (4′′-OCH3), 110.4 (C-6′′), 111.0 (C-5′′), 117.3 (C-5′), 117.7 (C-10), 118.7 and 118.8 (C-3′, C-1′), 119.6 (C-14a), 120.9 (C-2′′), 123.5 (C-13a), 124.9 (C-12), 126.0 (C-13), 129.4 (C-6′), 131.8 (C-1′′), 133.0 (C-4′), 133.5 (C-11), 149.0 and 149.7 (C-3′′, C-4′′), 155.8 (C-9a), 161.9 (C-8a), 164.8 (C-2′), 175.5 (C-14), 176.9 (C-2). HRMS-ESI+: m/z [M + H]+ calcd for C30H29N2O5: 497.2076; found: 497.2181
- 16 Crystal Data for Compound 2a C29H26N2O4, M = 466.52, monoclinic, space group P2 1 /c, Z = 4, a = 12.5174(10) Å, b = 7.8181(7) Å, c = 23.6772(19) Å, β = 101.434(2)°, V = 2271.1(3) Å3, μ(Mo-Kα) = 0.091 mm–1, D c = 1.364 mg cm–3, yellow block, crystal size: 0.13 × 0.05 × 0.04 mm3. Of a total of 42512 reflections collected, 4132 were independent (R int = 0.0442). Final R1 = 0.0507 [I > 2σ(I)] and wR2 = 0.1176 (all data). Data completeness to θ = 25.24°, 99.7%.
- 17 Crystal Data for Compound 2c C28H24N2O3, M = 436.49, monoclinic, space group P2 1 /c, Z = 4, a = 10.031(2) Å, b = 21.574(5) Å, c = 10.477(2) Å, β = 108.640(5)°, V = 2148.4(8) Å3, μ(Mo-Kα) = 0.088 mm–1, D c = 1.349 mg cm–3, colorless plates, crystal size: 0.17 × 0.09 × 0.04 mm3. Of a total of 24116 reflections collected, 3899 were independent (R int = 0.0375). Final R1 = 0.0528 [I > 2σ(I)] and wR2 = 0.1393 (all data). Data completeness to θ = 25.24°, 99.0%.
- 18 CCDC 1584431 and 1584430 contain the supplementary crystallographic data for compounds 2a and 2c, respectively. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.