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Synlett 2019; 30(15): 1782-1786
DOI: 10.1055/s-0039-1690189
DOI: 10.1055/s-0039-1690189
letter
Synthesis of Tetrahydropyrazolo[4',3':5,6]pyrano[3,4-c]quinolones by Domino Knoevenagel/Hetero Diels–Alder Reactions
Further Information
Publication History
Received: 25 June 2019
Accepted after revision: 06 August 2019
Publication Date:
14 August 2019 (online)
Abstract
An efficient Lewis acid mediated domino Knoevenagel/hetero Diels–Alder (DKHDA) reaction of pyrazolone derivatives with N-acrylated anthranilic aldehydes was developed, which afforded functionalized tetracyclic tetrahydropyrazolo[4',3':5,6]pyrano[3,4-c]quinolones. The products were formed in good yields and with excellent regio- and stereoselectivity in favor of the cis-configured isomer.
Key words
domino reaction - regioselectivity - cyclizations - heterocycles - Diels–Alder reaction - Knoevenagel reactionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690189.
- Supporting Information
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References and Notes
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- 32 Synthesis of Products 3a–h by DKHDA Reaction; General Procedure A mixture of N-acrylated anthranilaldehyde 1 (0.5 mmol), N-phenyl pyrazolone 2 (0.5 mmol), and ZnBr2 (50 mol%) was stirred in EtOH heated to reflux (5 mL). The progress of the reaction was followed by TLC. After completion (5 h) and cooling down, ice-cold water (20 mL) was poured into the reaction mixture. The resulting precipitate was filtered after stirring for 5 min and washed with cold water. After air drying at room temperature, the pure product 3 was obtained by column chromatography on silica gel, by eluting with n-hexane/ethyl acetate (2:1). (5R*,5aS*,11bS*)-7-Ethyl-1,5-dimethyl-3-phenyl-5,5a,7,11b-tetrahydropyrazolo[4',3':5,6]pyrano[3,4-c]quinolin-6(3H)-one (3d) Pale yellow solid; yield: 84% (157 mg); mp 180–182 °C. IR (ATR): 3066, 2930, 1664, 1599, 1496, 1126, 757 cm–1. 1H NMR (300 MHz, CDCl3): δ = 1.24 (t, J = 6.4 Hz, 3 H, CH3), 1.49 (d, J = 6.5 Hz, 3 H, CH3), 2.17 (s, 3 H, CH3), 2.84 (dd, J = 7.3, 5.2 Hz, 1 H, Hb), 3.88–4.03 (m, 3 H, Ha, NCH2), 4.25 (d, J = 5.1 Hz, 1 H, Hc), 7.02–7.21 (m, 3 H, Ar-H), 7.27–7.40 (m, 4 H, Ar-H), 7.73 (d, J = 8.51 Hz, 2 H, Ar-H). 13C NMR (75 MHz, CDCl3): δ = 12.7 (CH3), 13.4 (CH3), 18.8 (CH3), 31.0 (CH), 38.0 (NCH2), 46.3 (CH), 72.4 (OCH), 115.0 (CH), 120.3 (CH), 121.1 (C), 123.3 (CH), 125.6 (CH), 128.3 (CH), 128.9 (CH), 129.1 (CH), 129.8 (C), 137.4 (C), 138.5 (C), 146.8 (C), 149.4 (C), 167.2 (CON). HRMS (EI): m/z calcd for C23H23N3O2 [M]+: 373.1785; found: 373.1781.