- Synthesis and differential functionalisation of pyrrolidine and piperidine based spirodiamine scaffolds
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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.
- Weinberg, Kamil,Stoit, Axel,Kruse, Chris G.,Haddow, Mairi F.,Gallagher, Timothy
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p. 4694 - 4707
(2013/07/04)
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- Quinolone Antibacterial Agents Substituted at the 7-Position with Spiroamines. Synthesis and Structure-Activity Relationships
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A series of fluoroquinolone antibacterials having the 7-position (10-position of pyridobenzoxazines) substituted with 2,7-diazaspirononane (4b), 1,7-diazaspirononane (5a), or 2,8-diazaspiroundecane (6b) was prepared, and their biological activities were compared with piperazine and pyrrolidine substituted analogues.Most exhibited potent Gram-positive and Gram-negative activity, especially when side chain 4b was N-alkylated.
- Culbertson, Townley P.,Sanchez, Joseph P.,Gambino, Laura,Sesnie, Josephine A.
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p. 2270 - 2275
(2007/10/02)
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