Abstract
Synthesis of thiamacrocyclic bisamides incorporating bipyridine subunit tethered to poly(ethylene glycol) chains has been achieved using sequential S-transalkylation-amidification of 2,2'-bipyridine alkyl sulfides.
Highlights
Macrocyclic ligands containing amide functional groups play an important role in coordinationand supramolecular chemistry
There are a number of macrocycles which in addition to amide functional groups contain other elements and/or heteroaromatic rings
The synthetic pathway leading to macrocycles 2a,b and 3a,b starts with 2,2’-bipyridine methyl sulfides 4a and 4b readily prepared using literature procedures, namely Diels-Alder/retro- DielsAlder reaction of accessible 3,3’-bis(methylsulfanyl)-5,5’-bi-1,2,4-triazine with norbornadiene[8] or 1-pyrrolidino-1-cyclopentene,[9] respectively
Summary
Macrocyclic ligands containing amide functional groups play an important role in coordinationand supramolecular chemistry. Leading to 2,2’-bipyridine thiacrown ethers 2a,b and 3a,b (Figure 1) containing bisamide functional groups, using as the key steps: (1) S-transalkylation of 6,6’-bis(methylsulfanyl)-2,2’- The synthetic pathway leading to macrocycles 2a,b and 3a,b starts with 2,2’-bipyridine methyl sulfides 4a and 4b readily prepared using literature procedures, namely Diels-Alder/retro- DielsAlder reaction of accessible 3,3’-bis(methylsulfanyl)-5,5’-bi-1,2,4-triazine with norbornadiene[8] or 1-pyrrolidino-1-cyclopentene,[9] respectively.
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