期刊
JOURNAL OF THE CHINESE CHEMICAL SOCIETY
卷 66, 期 2, 页码 218-225出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/jccs.201800115
关键词
biological; indole; pyrimidine; synthesis
Pyrimidines and pyrimidine bearing indole derivatives are very important species in organic chemistry due to their wide use as bioactive compounds with a broad range of good biological activities. Due to the wide spread of different species of bacteria and fungi nowadays, in the present work, a novel series of indolyl-pyrimidines (2-13) were synthesized starting from 3-chloro-1H-indole-2-carbaldehyde (1). Elemental analysis, IR, 1H-NMR, 13C-NMR, and mass spectral data elucidated the structure of newly synthesized compounds. All compounds were screened for their in vitro antibacterial and antifungal activity, and they demonstrated promising results; all the new compounds synthesized from compound (1), which allowed reactions with thiourea and ethyl cyanoacetate, gave the target compound (2), which was used as a precursor for the synthesis of indolylthiazolopyrimidine derivatives (3-8) by reactions with halocarbonyl compounds such as chloroacetone, phancyl bromide, and chloroacetic acid through alkylation of the mercapto group followed by cyclization through a nucleophilic attack. When compound (2) subjected to react with hydrazine hydrate gave 4-indolyl-2-hydrazinopyrimidine (5), the latter compound, when allowed to react with ethyl chloroacetate or diethyloxalate, gave indolylpyrimidotriazine derivatives (10,11); in contrast, when the compound reacted with acetic anhydride or formic acid, it gave triazolopyrimidine derivatives (12, 13).
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