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Synthesis of Spiro{pyrrolidine‐3,1′‐pyrrolo[3,4‐ c ]pyrrole} Basic Framework by Multicomponent 1,3‐Dipolar Cycloaddition
Author(s) -
Belabbes Asmaa,
Selva Verónica,
Foubelo Francisco,
De Gracia Retamosa M.,
Sansano José M.
Publication year - 2021
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.202100646
Subject(s) - maleimide , pyrrolidine , chemistry , pyrrole , allylic rearrangement , cycloaddition , amine gas treating , metathesis , aldehyde , salt metathesis reaction , molecule , combinatorial chemistry , organic chemistry , catalysis , polymerization , polymer
The synthesis of the complex spiro{pyrrolidine‐3,1′‐pyrrolo[3,4‐c]pyrrole} skeleton under mild conditions is presented. The order of addition of a primary amine, two equivalents of the corresponding maleimide and, finally, the aldehyde is of a paramount importance to obtain these final compounds in very high yields. The mechanism was studied by performing very simple tests, the Michael type addition of the amine onto the maleimide being the key step. Interestingly, the hybrid scaffold was prepared by sequential addition of two different maleimides. In addition, a more interesting architecture was prepared through a metathesis reaction between allylic residues bonded in the molecule precursor.