Abstract
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 language | English (US) |
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Pages (from-to) | 10165-10171 |
Number of pages | 7 |
Journal | Tetrahedron |
Volume | 59 |
Issue number | 51 |
DOIs | |
State | Published - Dec 15 2003 |
Keywords
- Polyamines
- Polyazamacrocycles
- Protecting groups
- Sulfonamides