Synthesis of a new 24-membered tetramide macrocycle and X-ray crystal structure determination

[Display omitted] •A new 24-membered tetramide macrocycle has been prepared starting from m-xylylene diamine.•1H, 13C and 15N NMR characterization confirmed its structure.•The X-ray crystal structure of the macrocycle proved to be a dimethylsulfoxide solvate. The synthesis and characterization of a...

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Bibliographic Details
Published inTetrahedron letters Vol. 60; no. 17; pp. 1206 - 1209
Main Authors Santa María, Dolores, Claramunt, Rosa M., Torralba, M. Carmen, Torres, M. Rosario, Elguero, José
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 25.04.2019
Elsevier
Subjects
Amides
Chemistry
Chemistry, Organic
Inclusion compounds
Macrocycles
Physical Sciences
Science & Technology
X-ray
Amides
X-ray
Macrocycles
Inclusion compounds
AMIDE
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Summary:[Display omitted] •A new 24-membered tetramide macrocycle has been prepared starting from m-xylylene diamine.•1H, 13C and 15N NMR characterization confirmed its structure.•The X-ray crystal structure of the macrocycle proved to be a dimethylsulfoxide solvate. The synthesis and characterization of a new 24-membered tetramide macrocycle (6) related to Leigh's macrocycles and catenanes is reported. The replacement of p-xylylenediamine (Leigh) by m-xylylenediamine (this work) strongly modifies the geometry and properties of the new macrocycle. NMR spectroscopy (in DMSO‑d6 solution) and X-ray crystallography have been used to characterize compound 6. The structural features in the crystal (conformational aspects and H-bonding) have been discussed comparatively to two similar macrocycles NEWHIJ and UJUNOC.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2019.03.066