10.1021/ol402301g.s001
Jens Cordes
Jens
Cordes
Philip R. D. Murray
Philip
R. D. Murray
Andrew J. P. White
Andrew
J. P. White
Anthony G. M. Barrett
Anthony
G. M. Barrett
1,7-Diazaspiro[5.5]undecane – A Neglected Heterocycle
American Chemical Society
2013
spirocyclic adducts
alkyl halides
spirocyclization
decarboxylation
Claisen condensation
spiroaminal
Neglected HeterocycleA
Diazaspiro
step synthesis
complex
alkane dihalides
novel bidentate ligand
electrophile
tetrahydropyridine derivatives
ruthenium
acid chlorides
diazaspiro
sulfonyl chlorides
parent heterocycle
2013-10-04 00:00:00
Dataset
https://acs.figshare.com/articles/dataset/1_7_Diazaspiro_5_5_undecane_A_Neglected_Heterocycle/2370322
A convenient and simple three step synthesis of 1,7-diazaspiro[5.5]undecane via Claisen condensation and acid catalyzed decarboxylation and spirocyclization of <i>N</i>-Boc-δ-valerolactam is described. Reactions of this spiroaminal with electrophiles including alkyl halides, alkane dihalides, acid chlorides, and sulfonyl chlorides gave either spirocyclic adducts or tetrahydropyridine derivatives. Additionally, the parent heterocycle is a novel bidentate ligand and formed complexes with ruthenium(II) and copper(II).