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Synlett 2014; 25(2): 255-260
DOI: 10.1055/s-0033-1340288
DOI: 10.1055/s-0033-1340288
letter
Synthesis of 2-Acylbenzothiazoles via the Cu(OTf)2-Catalyzed Tandem Reaction of β,β-Dihalidestyrenes with 2,2′-Disulfanediyldianilines
Further Information
Publication History
Received: 21 August 2013
Accepted after revision: 17 October 2013
Publication Date:
03 December 2013 (online)
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Abstract
A new method has been developed for the one-pot construction of 2-acylbenzothiazoles via the Cu(OTf)2-catalyzed tandem reaction of β,β-dihalidestyrenes with 2,2′-disulfane-diyldianilines. A variety of different dihalidestyrenes and diphenyldisulfanes were efficiently converted into the corresponding 2-acylbenzothiszole derivatives in the presence of Cu(OTf)2. Most importantly, this protocol allowed for the long chain 1,1-dibromohept-1-ene to be converted into the corresponding 2-hexylbenzo[d]thiazole in moderate yield.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
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References and Notes
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- 13 To a Schlenk tube were added a mixture of β,β-dibromo-styrene 1a (0.2 mmol) and 2,2′-disulfanediyldianiline 2a (0.4 mmol), Cu(OTf)2 (10 mol%), Cs2CO3 (2 equiv), and DMSO (2 mL). Then the mixture was stirred at 120 °C for the indicated time until complete consumption of starting material as monitored by TLC and GC–MS analysis. After the reaction was finished, the mixture was washed with brine. The aqueous phase was re-extracted with Et2O. The combined organic extracts were dried over Na2SO4 and concentrated under vacuum, and the resulting residue was purified by silica gel column chromatography (hexane–EtOAc) to afford the target product 3. Benzo[d]thiazol-2-yl(4-methoxyphenyl)methanone (3): white solid; mp 120–122 °C. 1H NMR (500 MHz, CDCl3): δ = 8.58 (d, J = 9.0 Hz, 2 H), 8.17 (d, J = 8.0 Hz, 1 H), 7.94 (d, J = 8.0 Hz, 1 H), 7.47–7.51 (m, 2 H), 6.98 (d, J = 9.0 Hz, 2 H), 3.85 (s, 3 H). 13C NMR (125 MHz, CDCl3): δ = 183.4, 167.9, 164.4, 153.9, 136.9, 133.8, 127.8, 127.4, 126.8, 125.5, 122.1, 113.9, 55.6. LRMS (EI, 70 eV): m/z (%) = 269 (21) [M+], 241 (13), 135 (100), 107 (13), 92 (16), 77 (23).
For recent paper of synthesis of 2-acylbenzothiazoles, see: