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Synlett 2018; 29(11): 1437-1440
DOI: 10.1055/s-0037-1609684
letter
© Georg Thieme Verlag Stuttgart · New York

Catalyst-Free One-Pot Synthesis of Chromeno-Imidazo-Pyridinones by an Aza-Michael Addition/Rearrangement/Heterocyclization Tandem Reaction

Houria Lakhdari
a   Lab. de Chimie Organique Appliquée, Faculté de Chimie, Université des Sciences et de la Technologie Houari Boumediène BP 32, El-Alia Bab-Ezzouar, 16111 Alger, Algeria   Email: noraoussaid@yahoo.fr
b   Centre de Recherche Scientifique et Technique en Analyses Physico-Chimiques (CRAPC), BP 384, Bou-Ismail, 42004 Tipaza, Algeria   Email: oualid.talhi@ua.pt
,
Oualid Talhi*
b   Centre de Recherche Scientifique et Technique en Analyses Physico-Chimiques (CRAPC), BP 384, Bou-Ismail, 42004 Tipaza, Algeria   Email: oualid.talhi@ua.pt
d   QOPNA and Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal   Email: artur.silva@ua.pt
,
Ridha Hassaine
b   Centre de Recherche Scientifique et Technique en Analyses Physico-Chimiques (CRAPC), BP 384, Bou-Ismail, 42004 Tipaza, Algeria   Email: oualid.talhi@ua.pt
c   Lab. de Catalyse et Synthèse en Chimie Organique, Faculté des Sciences, Université de Tlemcen, BP 119, 13000 Tlemcen, Algeria
,
Nadia Taibi
b   Centre de Recherche Scientifique et Technique en Analyses Physico-Chimiques (CRAPC), BP 384, Bou-Ismail, 42004 Tipaza, Algeria   Email: oualid.talhi@ua.pt
,
Ricardo F. Mendes
e   CICECO–Aveiro Institute of Materials, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal
,
Filipe A. Almeida Paz
e   CICECO–Aveiro Institute of Materials, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal
,
Norah Bennamane*
a   Lab. de Chimie Organique Appliquée, Faculté de Chimie, Université des Sciences et de la Technologie Houari Boumediène BP 32, El-Alia Bab-Ezzouar, 16111 Alger, Algeria   Email: noraoussaid@yahoo.fr
,
Bellara Nedjar-Kolli
a   Lab. de Chimie Organique Appliquée, Faculté de Chimie, Université des Sciences et de la Technologie Houari Boumediène BP 32, El-Alia Bab-Ezzouar, 16111 Alger, Algeria   Email: noraoussaid@yahoo.fr
,
Khaldoun Bachari
b   Centre de Recherche Scientifique et Technique en Analyses Physico-Chimiques (CRAPC), BP 384, Bou-Ismail, 42004 Tipaza, Algeria   Email: oualid.talhi@ua.pt
,
Artur M. S. Silva  *
d   QOPNA and Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal   Email: artur.silva@ua.pt
› Author AffiliationsThanks are due to University of Aveiro and FCT/MEC for the financial support of 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: 13 January 2018

Accepted after revision: 20 March 2018

Publication Date:
07 May 2018 (online)

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Abstract

A one-pot synthesis of a novel series of chromeno-imidazo-pyridinone derivatives from 3-[(2-hydroxyphenyl)-3-oxoprop-1-en-1-yl]chromones and ethane-1,2-diamine at room temperature under catalyst-free conditions has been successfully developed. This approach involves a tandem aza-Michael addition reaction, a chromone-to-chromanone rearrangement, and a heterocyclization sequence, leading to chromeno-imidazo-pyridinone polyheterocycles. The structure and absolute configurations of the new compounds were elucidated by a combination of 1D- and 2D-NMR analyses and single-crystal X-ray diffraction.

Key words

chromones - ethanediamine - chromeno-imidazo-pyridinones - one-pot synthesis - tandem reaction - aza-Michael addition

Supporting Information

 

  • References and Notes

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  • 7 Chromeno-imidazo-pyridinones 2a–e; General Procedure H2N(CH2)2NH2 (10 mmol) was added to a stirred solution of the appropriate chromone 1a–e (1 mmol) in THF (20 mL), and the mixture was stirred for 24 h at r.t. The solvent was then removed under vacuum, and acetone (20 mL) was added to precipitate the solid product, which was collected by filtration and washed with acetone (×2) to afford the yellowish solid product. Good-quality single-crystals suitable for X-ray analysis were obtained only for compound 2a.
  • 8 12a-(2-Hydroxyphenyl)-1,2,3,11a,12,12a-hexahydro-6H-chromeno[2,3-d]imidazo[1,2-a]pyridin-6-one (2a) C20H18N2O3. Colorless crystals; yield: 0.28 g (84%); mp 237–239 °C. 1H NMR (300.13 MHz, DMSO-d6): δ = 2.15–2.34 (m, 1 H, H-2), 2.64–2.83 (m, 2 H, H-2, H12), 3.49–3.73 (m, 3 H, H-12, 2 × H-3), 4.52 (br s, 1 H, 1-NH), 4.66 (dd, J 10.8, 5.4 Hz, 1 H, H-11a), 6.69–6.83 (m, 3 H, H-3′, H-5′, H-6′), 6.88 (d, J 8.4 Hz, 1 H, H-10), 6.96–7.07 (m, 1 H, H-8), 7.11–7.22 (m, 1 H, H-4′), 7.33–7.44 (m, 1 H, H-9), 7.69–7.78 (m, 1 H, H-7), 8.06 (s, 1 H, H-5), 11.17 (br s, 1 H, 2′-OH). 13C NMR (75.47 MHz, DMSO-d6): δ = 36.0 (C-2), 42.6 (C-12), 48.3 (C-3), 71.3 (C-11a), 79.6 (C-12a), 102.1 (C-5a), 117.0 and 117.1 (C-3′ and C-10), 118.8 (C-5′), 121.5 (C-8), 123.7 (C-6a), 124.6 (C-1′), 126.1 (C-7), 126.7 (C-6′), 129.9 (C-4′), 133.6 (C-9), 142.0 (C-5), 154.5 (C-2′), 159.2 (C-10a), 176.0 (C-6). HRMS-ESI+: m/z [M + H]+ calcd for C20H19N2O3: 335.1396; found: 335.1380.
  • 9 12a-(2-Hydroxyphenyl)-8-methyl-1,2,3,11a,12,12a-hexahydro-6H-chromeno[2,3-d]imidazo[1,2-a]pyridin-6-one (2b) C21H20N2O3. Yellowish solid; yield: 0.27 g (77%); mp 255–256 °C. 1H NMR (300.13 MHz, DMSO-d6): δ = 2.25 (s, 3 H, 8-CH 3), 2.14–2.32 (m, 1 H, H-2), 2.63–2.85 (m, 2 H, H-2, H12), 3.36–3.40 (m, 1 H, H-12), 3.53–3.73 (m, 2 H, H-3), 4.55 (br s, 1 H, 1-NH), 4.61 (dd, J 10.8, 5.1 Hz, 1 H, H-11a), 6.69–6.82 (m, 4 H, H-3′, H-5′, H-6′, H-10), 7.12–7.23 (m, 2 H, H-4′, H-9), 7.53 (d, J 2.1 Hz, 1 H, H-7), 8.04 (s, 1 H, H-5), 11.59 (br s, 1 H, 2′-OH). 13C NMR (75.47 MHz, DMSO-d6): δ = 20.2 (8-CH3), 36.1 (C-2), 42.7 (C-12), 48.4 (C-3), 71.3 (C-11a), 79.6 (C-12a), 102.4 (C-5a), 116.9 and 117.1 (C-3′ and C-10), 118.9 (C-5′), 123.4 (C-6a), 124.7 (C-1′), 126.1 (C-7), 126.8 (C-6′), 129.9 (C-4′), 130.5 (C-8), 134.3 (C-9), 141.9 (C-5), 154.5 (C-2′), 157.3 (C-10a), 176.3 (C-6). HRMS-ESI+: m/z [M + H]+ calcd for C21H21N2O3: 349.1552; found: 349.1577.
  • 10 Crystal data for compound 2a: C20H18N2O3, M = 334.36, triclinic, space group P-1, Z = 2, a = 6.8074(7) Å, b = 10.1451(12) Å, c = 11.6511(12) Å, α = 86.729(4)º, β = 79.432(4)°, γ = 89.888(4)°, V = 789.68(15) Å3, μ(Mo-Kα) = 0.096 mm–1, D c = 1.406 mg/cm3, colorless needle, crystal size = 0.22 × 0.08 × 0.08 mm3. Of a total of 13735 reflections collected, 4159 were independent (R int = 0.0590). Final R1 = 0.0589 [I > 2σ(I)] and wR2 = 0.1666 (all data). Data completeness to θ = 25.24°, 99.2%.
  • 11 CCDC 1813216 contains the supplementary crystallographic data for compound 2a. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.