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2-Amidinylindole-3-carbaldehydes: Versatile Synthons for the Preparation of α-Carboline Derivatives

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
56
Issue
51
Identifiers
DOI: 10.1016/s0040-4020(00)00950-9
Keywords
  • 5-Amino-V-Triazolines
  • Amidines
  • α-Carboline
  • Pyrido[2
  • 3-B]Indole

Abstract

Abstract The 2-amidinylindole-3-carbaldehydes 1 are the key starting materials for the preparation of three classes of carbolines 2, 6 and 7 in which the pyridine ring is characterised by a different substitution patterns. The carbolines 2 which are functionalized with an amino group in position 2, were obtained directly by heating 1 in presence of SiO 2. The condensation of amidines 1 with arylmethylketones afforded unsaturated ketones 5 which on heating were transformed into 2,9-dialkyl-3-aroyl-9 H-pyrido[2,3- b]indoles 7. Instead, prolonged reaction of amidines 1 with arylmethylketones in t-BuOH/ t-BuOK gave 2-aryl-9 H-pyrido[2,3- b]indoles 6.

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