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Reactivity of 1,2‐Diaza‐1,3‐dienes with Azomethine Ylides: [3+4] versus [3+2] Cycloadditions
Author(s) -
Mantenuto Serena,
Cayuelas Alberto,
Favi Gianfranco,
Attanasi Orazio A.,
Mantellini Fabio,
Nájera Carmen,
Sansano José M.
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600640
Subject(s) - cycloaddition , chemistry , regioselectivity , moiety , reactivity (psychology) , 1,3 dipolar cycloaddition , polar effect , azomethine ylide , medicinal chemistry , stereochemistry , diene , organic chemistry , catalysis , medicine , natural rubber , alternative medicine , pathology
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 [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.
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