Application of alkyl 3-dimethylamino-2-(1 H-indol-3-yl)propenoates in the synthesis of 3-heteroarylindoles

Methyl and ethyl 3-dimethylamino-2-(indol-3-yl)propenoate were prepared from alkyl 3-indoleacetates and tert-butoxy-bis(dimethylamino)methane. Upon treatment of these two N, N-dimethylenaminones with α-heteroarylamines as N, N-1,3-dinucleophiles, condensed indolylpyrimidones as meridianine analogues...

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Bibliographic Details
Published in:Tetrahedron 2004-05, Vol.60 (21), p.4601-4608
Main Authors: Jakše, Renata, Svete, Jurij, Stanovnik, Branko, Golobič, Amalija
Format: Article
Language:English
Subjects:
Alkaloids
Enaminones
Heterocycles
Meridianines
Natural products
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Summary:Methyl and ethyl 3-dimethylamino-2-(indol-3-yl)propenoate were prepared from alkyl 3-indoleacetates and tert-butoxy-bis(dimethylamino)methane. Upon treatment of these two N, N-dimethylenaminones with α-heteroarylamines as N, N-1,3-dinucleophiles, condensed indolylpyrimidones as meridianine analogues were obtained in poor to moderate yields, while intramolecular condensations with C, O-1,3-dinucleophiles furnished condensed indolylpyranones. Similarly, reaction with hydrazinium chloride led to indolylpyrazolol, while with 3-chloro-6-hydrazinopyridazine only the dimethylamine substitution took place to give the corresponding hydrazone. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2004.03.075