The multicomponent 1,3-dipolar cycloaddition of different 1,2-diaza-1,3-dienes with in situ-generated azomethine ylides produces 1,2,4-triazepines or pyrrolidines by means of [3+4] or [3+2] cycloadditions, respectively. The regioselectivity is controlled by the electron-withdrawing group bound to the azo-moiety of the 1,2-diaza-1,3-diene which promotes exclusively the [3+4] cycloaddition. When the electron-withdrawing group is replaced with a phenyl group only a [3+2] cycloaddition occurs.
Reactivity of 1,2-diaza-1,3-dienes with azomethine ylides: [3+4] versus [3+2] cycloadditions
MANTENUTO, SERENA;FAVI, GIANFRANCO;ATTANASI, ORAZIO ANTONIO;MANTELLINI, FABIO;
2016
Abstract
The multicomponent 1,3-dipolar cycloaddition of different 1,2-diaza-1,3-dienes with in situ-generated azomethine ylides produces 1,2,4-triazepines or pyrrolidines by means of [3+4] or [3+2] cycloadditions, respectively. The regioselectivity is controlled by the electron-withdrawing group bound to the azo-moiety of the 1,2-diaza-1,3-diene which promotes exclusively the [3+4] cycloaddition. When the electron-withdrawing group is replaced with a phenyl group only a [3+2] cycloaddition occurs.File in questo prodotto:
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