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

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 obta...

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Bibliographic Details
Published in:Tetrahedron 2000-12, Vol.56 (51), p.9991-9997
Main Authors: Erba, Emanuela, Luisa Gelmi, M, Pocar, Donato
Format: Article
Language:English
Subjects:
5-amino- v-triazolines
amidines
pyrido[2,3- b]indole
α-carboline
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Summary: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.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(00)00950-9