Abstract
A one-pot tandem approach for the synthesis of benzothiazoles
from benzyl halides and o -aminobenzenethiol
was described. Benzothiazoles were obtained in high chemical yields under
mild conditions in DMSO in the absence of an additional oxidant.
Both benzyl chlorides and bromides bearing a range of substituents
proved to be suitable substrates.
Key words
benzothiazole - benzyl halide - oxidation - one-pot - tandem reaction
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13 Treatment of benzaldehyde with o -aminothiophenol under the same reaction
conditions gave the corresponding benzothiazole in 80% yield.
14
o -Aminophenol
was not a suitable substrate and the corresponding benzoxazole was
furnished in low yield under the same conditions.
15
General Experimental
Procedure
A mixture of benzyl halide (0.24 mmol, 1.2
equiv) with NaHCO3 (1 mmol, 5.0 equiv) in DMSO (2 mL)
was stirred for 5 h at 90 ˚C. Then, o -aminothiophenol
(0.2 mmol, 1.0 equiv) was added into the above solution. Resulting
solution was continued stirring for overnight up to the completion
of the reaction. The reaction mixture was cooled to r.t. and was extracted
with EtOAc. The combined organic layers were successively washed
with H2 O and brine, dried over anhyd Na2 SO4 ,
and concentrated to dryness. The crude product was purified by preparative
TLC on silica gel to give the product.
