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Synlett 2018; 29(07): 885-889
DOI: 10.1055/s-0037-1609201
letter
© Georg Thieme Verlag Stuttgart · New York

Diastereoselective One-Pot Tandem Synthesis of Chromenopyridodiazepinones through 1,4- and 1,6-Aza-Conjugate Additions/Heterocyclizations

Abdelghani Bouchama
a   Centre de Recherche Scientifique et Technique en Analyses Physico-Chimiques (CRAPC), BP 384, Bou-Ismail, 42004 Tipaza, Algeria
b   Laboratoire de Structure, Elaboration et Application des Matériaux Moléculaires (SEA2M), Faculté des Sciences et de la Technologie, BP 188, Université Abdelhamid Benbadis, Mostaganem, Algeria
,
Ridha Hassaine
a   Centre de Recherche Scientifique et Technique en Analyses Physico-Chimiques (CRAPC), BP 384, Bou-Ismail, 42004 Tipaza, Algeria
c   Laboratoire de Catalyse et Synthèse en Chimie Organique, Faculté des Sciences, Université de Tlemcen, BP 119, 13000 Tlemcen, Algeria
,
Oualid Talhi*
a   Centre de Recherche Scientifique et Technique en Analyses Physico-Chimiques (CRAPC), BP 384, Bou-Ismail, 42004 Tipaza, Algeria
d   QOPNA and Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal   Email: oualid.talhi@ua.pt   Email: artur.silva@ua.pt
,
Nadia Taibi
a   Centre de Recherche Scientifique et Technique en Analyses Physico-Chimiques (CRAPC), BP 384, Bou-Ismail, 42004 Tipaza, Algeria
,
Ricardo F. Mendes
e   CICECO - Aveiro Institute of Materials, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal
,
Fillipe A. Almeida Paz
e   CICECO - Aveiro Institute of Materials, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal
,
Khaldoun Bachari
a   Centre de Recherche Scientifique et Technique en Analyses Physico-Chimiques (CRAPC), BP 384, Bou-Ismail, 42004 Tipaza, Algeria
,
Artur M. S. Silva  *
d   QOPNA and Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal   Email: oualid.talhi@ua.pt   Email: artur.silva@ua.pt
› Author AffiliationsThanks 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)

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Diastereoselective One-Pot Tandem Synthesis of Chromeno­pyri­dodiazepinones through 1,4- and 1,6-Aza-Conjugate ­Additions/ HeterocyclizationsSynlett 2018; 29(07): ex-ex
DOI: 10.1055/s-0037-1609341

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 addition

Supporting Information

 

  • 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
      CrossrefPubMed
    • 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
      CrossrefPubMed
    • 2b Franke K. Porzel A. Schmidt J. Phytochemistry 2002; 61: 873
      CrossrefPubMed
    • 2c Toshima K. Kimura T. Takano R. Ozawa T. Ariga A. Shima Y. Umezawa K. Matsumura S. Tetrahedron 2003; 59: 7057
      Crossref
    • 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
      CrossrefPubMed
    • 2f Belluti F. Fontana G. Dal Bo L. Carenini N. Giommarelli C. Zunino F. Bioorg. Med. Chem. 2010; 18: 3543
      CrossrefPubMed
    • 2g Romanov VE. Shul’ts EE. Shakirov MM. Tolstikov GA. Dokl. Chem. (Engl. Transl.) 2010; 430: 27
      Crossref
    • 2h Belovodskii AV. Shul’ts EE. Shakirov MM. Romanov VE. Elmuradov BZ. Shakhidoyatov KM. Tolstikov GA. Chem. Nat. Compd. 2011; 46: 880
      Crossref
  • 3 Talhi O. Fernandes JA. Pinto DC. G. A. Almieda Paz FA. Silva AS. M. Tetrahedron 2013; 69: 5413
    Crossref
  • 4 Thurston DE. Bose DS. Chem. Rev. 1994; 94: 433
    Crossref
    • 5a Hsu MC. Schutt AD. Holly M. Slice LW. Sherman MI. Richman DD. Potash MJ. Volsky DJ. Science 1991; 254: 1799
      CrossrefPubMed
    • 5b De Clercq E. Antiviral Res. 1998; 38: 153
      CrossrefPubMed
    • 6a Gregson SJ. Howard PW. Corcoran KE. Jenkins TC. Kelland LR. Thurston DE. Bioorg. Med. Chem. Lett. 2001; 11: 2859
      CrossrefPubMed
    • 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
      CrossrefPubMed
    • 7a Kornecki E. Ehrlich YH. Lenox RH. Science 1984; 226: 1454
      CrossrefPubMed
    • 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
      CrossrefPubMed
    • 7d Lisowski V. Fabis F. Pierré A. Caignard DH. Renard P. Rault S. J. Enzym. Inhib. Med. Chem. 2002; 17: 403
      CrossrefPubMed
    • 8a Abrous L. Hynes JJr. Friederich SR. Smith AB. III. Hirschmann R. Org. Lett. 2001; 3: 1089
      CrossrefPubMed
    • 8b Surman MD. Mulvihill MJ. Miller MJ. Org. Lett. 2002; 4: 139
      CrossrefPubMed
    • 8c Herrero S. García-López MT. Herranz R. J. Org. Chem. 2003; 68: 4582
      CrossrefPubMed
    • 8d Beccalli EM. Broggini G. Paladino G. Pilati T. Pontremoli G. Tetrahedron: Asymmetry 2004; 15: 687
      Crossref
    • 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
      Crossref
    • 8f Hemming K. Loukou C. Tetrahedron 2004; 60: 3349
      Crossref
    • 8g De Silva RA. Santra S. Andreana PR. Org. Lett. 2008; 10: 4541
      CrossrefPubMed
    • 8h Shaabani A. Maleki A. Mofakham H. J. Comb. Chem. 2008; 10: 595
      CrossrefPubMed
    • 9a Beccalli EM. Broggini G. Paladino G. Zoni C. Tetrahedron 2005; 61: 61
      Crossref
    • 9b Legerén L. Domínguez D. Tetrahedron Lett. 2010; 51: 4053
      Crossref
    • 10a Canonne P. Akssira M. Dahdouh A. Kasmi H. Boumzebra M. Heterocycles 1993; 36: 1305
      Crossref
    • 10b El Bouakher A. Laborie H. Aadil M. El Hakmaoui A. Lazar S. Akssira M. Viaud-Massuard M.-C. Tetrahedron Lett. 2011; 52: 5077
      Crossref
    • 11a Price WA. Silva AM. S. Cavaleiro JA. S. Heterocycles 1993; 36: 2601
      Crossref
    • 11b Desideri N. Conti C. Mastromarino P. Mastropaolo F. Antiviral Chem. Chemother. 2000; 11: 373
      CrossrefPubMed
    • 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
      CrossrefPubMed
    • 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
      CrossrefPubMed
    • 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
      CrossrefPubMed
    • 11f Gomes A. Fernandes E. Silva AM. S. Pinto DC. G. A. Cavaleiro JA. S. Lima JL. F. C. Biochem. Pharmacol. 2009; 78: 171
      CrossrefPubMed
    • 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
      CrossrefPubMed
    • 11h Gomes A. Freitas M. Fernandes E. Lima JL. Mini-Rev. Med. Chem. 2010; 10: 1
      CrossrefPubMed
    • 11i Rocha-Pereira J. Cunha R. Pinto DC. G. A. Silva AM. S. São José Nascimento M. Bioorg. Med. Chem. 2010; 18: 4195
      CrossrefPubMed
    • 11j Yang C.-H. Yang Y. Liu J.-H. Phytochem. Lett. 2013; 6: 387
      Crossref
    • 11k Lin C. Lu P.-J. Yang C.-N. Hulme C.-A. Shaw Y. Med. Chem. Res. 2013; 22: 2385
      Crossref
    • 11l Pawar SP. Kondhare DD. Zubaidha PK. Med. Chem. Res. 2013; 22: 753
      Crossref
    • 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
      CrossrefPubMed
    • 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
      Crossref
    • 12b Hayashi Y. Okamura D. Umemiya S. Uchimaru T. ChemCatChem 2012; 4: 959
      Crossref
    • 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.