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Synlett 2015; 26(08): 1039-1044
DOI: 10.1055/s-0034-1380272
DOI: 10.1055/s-0034-1380272
letter
Copper(I) Iodide Supported Synthesis of Coumarin- and Quinolone-Annulated 2-Aminothiazoles
Further Information
Publication History
Received: 13 November 2014
Accepted after revision: 04 February 2015
Publication Date:
03 March 2015 (online)
Abstract
An efficient and convenient method for the synthesis of coumarin- and quinolone-annulated 2-aminothiazoles is reported. The fused ring 2-aminothiazoles were synthesized from substituted coumarin/quinoline and phenylisothiocyanates in the presence of CuI, DABCO, and 1,10-phenanthroline. Both the rings in coumarin moiety supported the annulation by this method.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380272.
- Supporting Information
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References and Notes
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- 15 Analytical Data 2-(Phenylamino)-7H-chromeno[6,5-d]thiazol-7-one (2a) Pale yellow solid; mp 260–262 °C; yield: 70%. IR: 1540, 1617, 1722, 2862, 3245 cm–1. 1H NMR (400 MHz, CDCl3): δ = 6.40 (d, J = 9.6 Hz, 1 H), 7.27 (d, J = 7.6 Hz, 1 H), 7.40 (d, J = 7.2 Hz, 2 H), 7.45 (d, J = 7.2 Hz, 1 H), 7.51–7.57 (m, 3 H), 7.71 (d, J = 8.8, 1 H), 10.46 (br s, 1 H). 13C NMR (100 MHz, CDCl3): δ = 112.35, 114.89, 116.55, 122.14, 127.90, 128.45, 128.51, 130.35, 140.86, 143.75, 149.54, 149.79, 160.73, 173.35: 6-Methyl-2-(phenylamino)thiazolo[5,4-f]quinolin-7(6H)-one (2d) Light brown solid; mp 288–290 °C; yield: 81%. IR: 1545, 1612, 1662, 2883, 3113 cm–1. 1H NMR (400 MHz, CDCl3): δ = 3.75 (s, 3 H), 6.69 (d, J = 9.2 Hz, 1 H), 7.31 (d, J = 8.8 Hz, 1 H), 7.40–7.45 (m, 3 H), 7.50–7.54 (m, 3 H), 7.77 (d, J = 9.2 Hz, 1 H), 10.24 (br s, 1 H). 13C NMR (100 MHz, CDCl3): δ = 29.84, 112.66, 114.33, 121.57, 121.98, 127.87, 128.33, 129.49, 130.28, 135.51, 135.85, 143.94, 148.24, 161.80, 169.01. 2-(Phenylamino)-4H-chromeno[3,4-d]thiazol-4-one (2f) Off-white solid; mp > 300 °C; yield: 64%. IR: 1541, 1616, 1722, 2850, 3109 cm–1. 1H NMR (400 MHz, CDCl3): δ = 7.18–7.24 (m, 2 H), 7.37–7.40 (m, 4 H), 7.46 (t, J = 7.6 Hz, 1 H), 7.54 (t, J = 7.6 Hz, 2 H), 10.22 (br s, 1 H).