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Rapid cleavage of cyclic tertiary amides of Kemp's triacid: effects of ring structure.

Abstract：

:The piperidyl and prolyl amides of Kemp's triacid (7 and 8, respectively) have been prepared and their rates of intramolecular acylolysis measured as a function of pD. The piperidyl derivative 7 reacts approximately four-times faster (e.g., t(1/2)=3 min at 20 degrees C and pD7.7) than the previously reported pyrrolidyl and methylphenethyl amide derivatives, while the prolyl derivative 8 reacts two-times more slowly (e.g., e.g., t(1/2)=30 min at 20 degrees C and pD7.8). Molecular-mechanics calculations indicate that the nonbonded interactions in the piperidyl derivative 7 are distinct from those in the prolyl, pyrrolidyl, and methylphenethyl amide derivatives, a result that supports the suggestion that ground-state pseudoallylic strain contributes to the enormous reactivity of Kemp's triacid tertiary amides. In sum, the results reported indicate that the Kemp's triacid scaffolding provides a general means of activating tertiary amide derivatives.

journal_name

Bioorg Med Chem Lett

journal_title

Bioorganic & medicinal chemistry letters

authors

Dougan ML,Chin JL,Solt K,Hansen DE

doi

10.1016/j.bmcl.2004.06.024

subject

Has Abstract

pub_date

2004-08-16 00:00:00

pages

4153-6

issue

16

eissn

0960-894X

issn

1464-3405

pii

S0960894X04007784

journal_volume

14

pub_type

杂志文章

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