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Towards the syntheses of N ‐H and N ‐alkylated derivatives of meridianins
Author(s) -
Corbel Bernard,
Michaud FrançOis,
Meijer Laurent,
Simon Gaëlle,
CouthonGourves Hélène,
Haelters JeanPierre,
Kervarec Nelly
Publication year - 2007
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570440407
Subject(s) - chemistry , alkylation , pyrrolidine , alkyl , tosyl , guanidine , nuclear magnetic resonance spectroscopy , medicinal chemistry , stereochemistry , organic chemistry , catalysis
Novel N ‐H and N ‐alkylated derivatives of meridianins have been synthesized as potential antitumor agents by a two‐step conversion of N ‐tosyl‐3‐acetylindoles or N ‐alkyl‐3‐acetylindoles to the corresponding enaminones using DMF‐DMA, with or without added pyrrolidine. Further cyclization with guanidine gave the corresponding 2‐aminopyrimidines. The structures of the compounds, thus obtained, were proved by 1 H and 13 C NMR spectroscopy, NOE experiments and X‐ray analysis.