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Synlett 2017; 28(17): 2291-2294
DOI: 10.1055/s-0036-1589065
DOI: 10.1055/s-0036-1589065
letter
One-Pot Synthesis of Unsymmetrical Bis(4-Hydroxycoumarin-3-yl)methanes
Further Information
Publication History
Received: 25 April 2017
Accepted after revision: 02 June 2017
Publication Date:
13 July 2017 (online)
Abstract
Unsymmetrical bis(4-hydroxycoumarin-3-yl)methane derivatives have been synthesized from 4-hydroxycoumarins, aldehydes, and secondary amines via 3-(aminoalkyl)-4-hydroxycoumarin intermediates, followed by substitution.
Supporting Information
- Supporting information for this article is available online at https://doi.org /10.1055/s-0036-1589065.
- Supporting Information
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- 25 -Hydroxy-3-[(4-hydroxy-2-oxo-2H-chromen-3-yl)(phenyl)methyl]-6-methyl-2H-chromen-2-one (6a); Typical Procedure Equimolar amounts of 4-hydroxycoumarin (1a; 0.162 g, 1 mmol), benzaldehyde (2a, 0.106 g, 1 mmol), and pyrrolidine (3; 0.071 g, 1mmol) in MeCN (5 mL) were stirred at r.t. for 2 h until the reaction was complete (TLC). During this period a precipitate appeared. 4-Hydroxy-6-methylcoumarin (5a; 0.176 g, 1 mmol) was added, and the mixture was reflux for 4.5 h until the reaction was complete (TLC). The mixture was cooled and the solid product was collected by filtration and crystallized (MeCN). The filtrate was diluted with hexane (20 mL) and passed through a short column of silica gel. The pyrrolidine that remained in the column was eluted with MeOH. Colorless crystalline solid; yield: 0.366 g (86%); mp 201 °C. IR (KBr) = 3158.6, 3023.0, 1609.2, 1649.1, 1560.3 cm–1. 1H NMR (500 MHz, DMSO-d 6): δ = 2.30 (s, 3 H), 6.16 (s, 1 H), 7.30–8.19 (m, 12 H), 11.58 (s, 2 H). 13C NMR (125 MHz, DMSO-d 6): δ = 20.8, 36.4, 103.8 (2C), 119.8, 119.9, 120.2, 120.3, 123.1, 125.1, 126.9 (2 C), 128.0 (2 C), 131.2, 131.9, 132.0, 132.1, 132.2, 142.8, 150.9, 152.8, 164.9 (2 C), 165.0 (2 C). HRMS (–ESI); m/z [M – H]– Calcd for C26H18O6: 425.1025; found: 425.1026.