An efficient cyclization of lapachol to new benzo[ h ]chromene hybrid compounds: a stepwise vs. one-pot esterification-click (CuAAC) study

A straightforward one-pot vs. stepwise esterification of lapachol was performed to obtain highly diversified heterocycles. Whereas the one-pot esterification leads to mono esterified lapachol, the stepwise approach generated benzo[ h ]chromene. Furthermore, benzo[ h ]chromene architectures with embe...

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Bibliographic Details
Published in:New journal of chemistry 2018, Vol.42 (24), p.19591-19599
Main Authors: F. de la Torre, Alexander, Ali, Akbar, Westermann, Bernhard, Schmeda-Hirschmann, Guillermo, Walter Pertino, Mariano
Format: Article
Language:English
Subjects:
Alkynes
Cycloaddition
Esterification
Mass spectra
NMR
Nuclear magnetic resonance
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Summary:A straightforward one-pot vs. stepwise esterification of lapachol was performed to obtain highly diversified heterocycles. Whereas the one-pot esterification leads to mono esterified lapachol, the stepwise approach generated benzo[ h ]chromene. Furthermore, benzo[ h ]chromene architectures with embedded triazole moieties were synthesized through late-stage functionalization of the benzo[ h ]chromene terminal alkyne moiety by copper catalyzed 1,3-dipolar cycloaddition (CuAAC) in a one-pot procedure.
ISSN:1144-0546
1369-9261
DOI:10.1039/C8NJ03699C