A practical method for building linear and cyclic triamines from (2-trimethylsilyl)ethanesulfonamides (SES-amides)

Laurie L. Parker, Nicholas D. Gowans, Stephen W. Jones, David J. Robins

Research output: Contribution to journalArticlepeer-review

14 Scopus citations


SES-chloride has been obtained in higher yield and purity by improving Weinreb's original procedure, allowing efficient access to the primary SES-amide. Linear triamines can be built conveniently from the SES-amide in high yields, with the potential for orthogonal protection. The modified Richman-Atkins cyclisation of SES-amides allows access to novel biologically interesting triazamacrocycles with combinations of three-, four-, five- and six-carbon bridges within the ring. Purification of the free macrocyclic amines by distillation greatly simplifies the workup, increasing the practicability of multi-gram scale synthesis. Although CsF sometimes provided undesirably low yields in the deprotection step, alternative fluoride sources were found to be unsuitable for the deprotection of SES-triazamacrocycles.

Original languageEnglish (US)
Pages (from-to)10165-10171
Number of pages7
Issue number51
StatePublished - Dec 15 2003


  • Polyamines
  • Polyazamacrocycles
  • Protecting groups
  • Sulfonamides


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