Synthesis of 2-Acylbenzothiazoles via the Cu(OTf)2-Catalyzed Tandem Reaction of β,β-Dihalidestyrenes with 2,2′-Disulfanediyldianilines

Zeng-Le Zhou; Tao Fang; Ri-Yuan Tang; Xing-Guo Zhang; Chen-Liang Deng

doi:10.1055/s-0033-1340288

Synlett, Table of Contents

Synlett 2014; 25(2): 255-260
DOI: 10.1055/s-0033-1340288

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Synthesis of 2-Acylbenzothiazoles via the Cu(OTf)₂-Catalyzed Tandem Reaction of β,β-Dihalidestyrenes with 2,2′-Disulfanediyldianilines

Zeng-Le Zhou

College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, P. R. of China Fax: +86(577)86689300 Email: dengchenliang78@tom.com

,

Tao Fang

College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, P. R. of China Fax: +86(577)86689300 Email: dengchenliang78@tom.com

,

Ri-Yuan Tang

College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, P. R. of China Fax: +86(577)86689300 Email: dengchenliang78@tom.com

,

Xing-Guo Zhang

College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, P. R. of China Fax: +86(577)86689300 Email: dengchenliang78@tom.com

,

Chen-Liang Deng*

College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, P. R. of China Fax: +86(577)86689300 Email: dengchenliang78@tom.com

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Abstract

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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.

Keywords

Cu(OTf)₂ - dihalidestyrene - diphenyldisulfane - 2-acylbenzothiazole - tandem reaction

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References

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).

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