New Convenient Synthesis of Fluorescent 1,8-Naphthyridines and the Metal-Sensing Properties of the Dyes

Atul Goel; Pankaj Nag; Shahida Umar

doi:10.1055/s-0033-1339113

Synlett, Table of Contents

Synlett 2014; 25(11): 1542-1546
DOI: 10.1055/s-0033-1339113

letter

New Convenient Synthesis of Fluorescent 1,8-Naphthyridines and the Metal-Sensing Properties of the Dyes

Atul Goel*

Division of Medicinal and Process Chemistry, CSIR-Central Drug Research Institute, Lucknow 226031, India Fax: +91(522)2771941 Email: atul_goel@cdri.res.in

,

Pankaj Nag

Division of Medicinal and Process Chemistry, CSIR-Central Drug Research Institute, Lucknow 226031, India Fax: +91(522)2771941 Email: atul_goel@cdri.res.in

,

Shahida Umar

Division of Medicinal and Process Chemistry, CSIR-Central Drug Research Institute, Lucknow 226031, India Fax: +91(522)2771941 Email: atul_goel@cdri.res.in

› Author Affiliations

Abstract

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Abstract

A new and efficient approach to a series of highly fluorescent non-aggregating donor–acceptor 1,8-naphthyridines is described. Examination of the photophysical properties of the 1,8-naphthyridines revealed that the presence of donor–acceptor functionality leads to bright green fluorescence with solvatochromism in solvents of differing polarities. The application of these molecules in metal sensing was also explored.

Key words

1,8-naphthyridines - lactones - non-aggregating - solvatochromism - metal sensing

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References

References and Notes

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18 Naphthyridines 6a–e and 8a–e; General Procedure A mixture of the appropriate carbonitrile 4a–e (1 mmol) with 1-(2-methyl-1,8-naphthyridin-3-yl)ethanone (5; 1.2 mmol) or 8,9-dihydrobenzo[b]-1,8-naphthyridin-6(7H)-one (7; 1.2 mmol) and KOH (1.5 mmol) in anhyd DMF (5 mL) was stirred at r.t. under N₂ for 25–30 min. When the reaction was complete (TLC), the mixture was poured onto crushed ice with vigorous stirring then neutralized with 10% aq HCl. The resulting precipitate was collected by filtration and purified by column chromatography (silica gel, CHCl₃–MeOH). 3-(2-Methyl-1,8-naphthyridin-3-yl)-5-piperidin-1-yl-biphenyl-4-carbonitrile (6a) Yellow solid; yield: 262 mg (65%); mp 130–132 °C (CHCl₃–MeOH); R_f = 0.54 (CHCl₃–MeOH, 24:1); IR (KBr): 2932 (s), 2852 (s), 2213 (s), 1656 (m), 1591 (m), 1553 (m) cm^–1; ¹H NMR (300 MHz, CDCl₃, TMS): δ = 1.52–1.96 (m, 6 H), 2.74 (s, 3 H), 3.19–3.42 (m, 4 H), 7.03–7.71 (m, 8 H), 7.98–8.30 (m, 2 H), 9.03–9.23 (m, 1 H); ¹³C NMR (75.5 MHz, CDCl₃): δ = 24.0, 24.4, 26.1, 53.4, 105.0, 116.9, 117.1, 120.8, 121.3, 121.9, 127.2, 128.8, 129.0, 133.9, 136.8, 137.4, 139.4, 144.8, 146.3, 153.8, 155.5, 158.2, 160.9; MS (ESI): m/z = 405 [M + H]⁺; HRMS: m/z [M + H]⁺ calcd for C₂₇H₂₅N₄: 405.2079; found: 405.2130. 4-Phenyl-2-piperidin-1-yl-5,6-dihydronaphtho[2,1-b]-1,8-naphthyridine-1-carbonitrile (8a) Yellow solid; yield: 257 mg (62%); mp 194–196 °C (CHCl₃–MeOH); R_f = 0.60 (CHCl₃–MeOH, 24:1); IR (KBr): 2939 (s), 2850 (w) 2214 (s), 1584 (s), 1443 (m) cm^–1; ¹H NMR (300 MHz, CDCl₃,TMS): δ = 1.48–1.72 (m, 2 H), 1.74–2.01 (m, 4 H), 2.67–3.02 (m, 2 H), 3.03–3.41 (m, 6 H), 7.00 (s, 1 H), 7.10–7.65 (m, 6 H), 8.31 (d, J = 6.2 Hz, 1 H), 8.90–9.25 (m, 2 H); ¹³C NMR (75.5 MHz, CDCl₃): δ = 23.9, 25.9, 26.1, 33.4, 53.8, 102.8, 119.1, 120.5, 121.7, 121.9, 127.0, 128.1, 128.5, 128.8, 130.7, 135.1, 137.5, 137.8, 139.9, 146.4, 153.8, 155.2, 157.7, 163.9; MS (ESI): m/z = 417 [M + H]⁺; HRMS: m/z [M + H]⁺ calcd for C₂₈H₂₅N₄: 417.2079; found: 417.2085.
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