Journal
ACTA CHIMICA SLOVENICA
Volume 68, Issue 2, Pages 404-413Publisher
SLOVENSKO KEMIJSKO DRUSTVO
DOI: 10.17344/acsi.2020.6466
Keywords
Triazoles; click reaction; internal aldol condensation; macrocyclic enones; anticancer activity
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Funding
- CSIR-New Delhi [02/247/15/EMR-II]
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In this study, macrocyclic enones were successfully synthesized starting from alkyl ether and triazole as a linker using click reaction and intramolecular aldol condensation. The newly synthesized macrocyclic enone demonstrated good reactivity as a dipolarophile in 1,3-dipolar cycloaddition and reacted with dipoles generated from hydrazine hydrochloride, hydroxylamine, and guanidine hydrochloride to form a new class of spiro aminopyrimidines, phenyl pyrazoles, and isoxazoles grafted macrocycles in good yield. The structures of the newly synthesized compounds were confirmed using IR, NMR, and mass spectroscopy and evaluated for their anti-cancer activity.
Synthesis of macrocylic enones starting from alkyl ether and triazole as a linker was achieved using click reaction and intramolecular aldol condensation. The newly synthesized macrocyclic enone was successfully utilized as a dipolarophile in 1,3-dipolar cycloaddition. The dipoles generated from hydrazine hydrochloride, hydroxylamine and guanidine hydrochloride were reacted with macrocyclic enone to give a new class of spiro aminopyrimidines, phenyl pyrazoles and isoxazoles grafted macrocycles in good yield. The structures of newly synthesized compounds were confirmed with IR, NMR and mass spectroscopy and evaluated for their anti cancer activity.
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