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A clay-mediated, regioselective synthesis of 2-(aryl/alkyl)amino-thiazolo[4,5-c]carbazoles

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
45
Issue
25
Identifiers
DOI: 10.1016/j.tetlet.2004.04.129
Keywords
  • Thiazolo[4
  • 5-C]Carbazoles
  • Regioselective Synthesis
  • Clay-Mediated

Abstract

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-benzylaminothiazolo[4,5- 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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