Heteroring-Annulated Pyrrolino-Tetrahydroberberine Analogues

A facile method for the synthesis of pyrrolino-tetrahydroberberine derivatives starting from 1,2-diaza-1,3-dienes and dihydroberberines is reported. The synthesis is a cascade reaction involving a Michael-type addition of the enamine moiety of dihydroberberine to an azo-ene system, followed by nitro...

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Bibliographic Details
Published inAsian journal of organic chemistry Vol. 6; no. 6; pp. 720 - 727
Main Authors Mari, Giacomo, De Crescentini, Lucia, Favi, Gianfranco, Lombardi, Paolo, Fiorillo, Gaetano, Giorgi, Gianluca, Mantellini, Fabio
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.06.2017
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Michael addition
3-OXOALKANAMIDES
ORGANIC-SYNTHESIS
CELLS
fused-ring systems
SITU GENERATED 1,2-DIAZA-1,3-DIENES
1,2-diaza-1,3-dienes
pyrrolino-tetrahydroberberines
CANCER
annulation
HETEROCYCLES
BERBERINE DERIVATIVES
PYRIDAZINES
METAL-IONS
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Summary:A facile method for the synthesis of pyrrolino-tetrahydroberberine derivatives starting from 1,2-diaza-1,3-dienes and dihydroberberines is reported. The synthesis is a cascade reaction involving a Michael-type addition of the enamine moiety of dihydroberberine to an azo-ene system, followed by nitrogen cyclization on the resulting iminium ion.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.201700051