A novel reaction between benzothiazoles and diaroylacetylenes in the presence of Meldrum’s acid: ring expansion of benzothiazoles to functionalized 1,4-benzothiazines |
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Authors: | Mehdi Adib Esmaeil Sheibani Hamid Reza Bijanzadeh |
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Affiliation: | a School of Chemistry, University College of Science, University of Tehran, PO Box 14155-6455, Tehran, Iran b Chemistry Department, Zhejiang University, Hangzhou 310027, PR of China c Department of Chemistry, Tarbiat Modarres University, PO Box 14115-175, Tehran, Iran |
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Abstract: | A novel and efficient ring expansion of benzothiazoles to functionalized 1,4-benzothiazines is described. The reactive 1:1 zwitterionic intermediates formed by addition of benzothiazoles to diaroylacetylenes were trapped with Meldrum’s acid under mild reaction conditions to produce 2-[2-hydroxy-2-aryl-2H-1,4-benzothiazin-3(4H)-yliden]-1-aryl-1-ethanones in excellent yields. |
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Keywords: | Diaroylacetylenes Benzothiazoles Ring expansion Meldrum&rsquo s acid |
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