Tetrahedron p. 4694 - 4707 (2013)
Update date:2022-08-03
Topics:
Weinberg, Kamil
Stoit, Axel
Kruse, Chris G.
Haddow, Mairi F.
Gallagher, Timothy
The synthesis and differential substitution/protection of a series of spirodiamine scaffolds are described. Methods for selective access to the two mono-N-methyl isomers based on 2,7-diazaspiro[4.5]decane are also described. Key precursors associated with this chemistry are prone to rearrangement and methods for circumventing this issue are reported. While direct mono-carbamoylation (Boc) was not efficient, selective deprotection of doubly Boc-protected derivatives derived from symmetrical diamines provided mono-Boc variants. N-Arylation, exemplified by a series of monosubstituted spirodiamines incorporating the 2-chloro-5-pyridyl moiety, which is a privileged nicotinic agonist substructure, has also been carried out to provide monoarylated secondary and tertiary spirodiamines variants.
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