A clay-mediated, regioselective synthesis of 2-(aryl/alkyl)amino-thiazolo[4,5-c]carbazoles |
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Authors: | Manas Chakrabarty Nandita Ghosh |
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Institution: | a Department of Chemistry, Bose Institute, 93/1, A.P.C. Road, Kolkata 700009, India b School of Pharmaceutical Sciences, Kitasato University, Minato-ku, Tokyo 108, Japan |
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Abstract: | The 3-aminocarbazoles 1a-e were condensed with phenyl and benzyl isothiocyanates on montmorillonite K10 clay or TLC-grade silica gel at room temperature to furnish efficiently the N-phenyl and N-benzylthioureidocarbazoles, 2a-e and 2f, respectively, within minutes. When adsorbed on montmorillonite K10 clay impregnated with para-toluene sulfonic acid (1:1, w/w) and heated at 60-70 °C, 2a-e and 2f furnished the 2-anilino and 2-benzylaminothiazolo4,5-c]carbazoles, 3a-e and 3f, respectively, regioselectively in high yields. The cyclisation was also effective for the N-methylthioureidocarbazoles 2g-i. |
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Keywords: | Thiazolo[4 5-c]carbazoles Regioselective synthesis Clay-mediated |
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