2020
DOI: 10.1039/c9ra08056b
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Efficient syntheses of macrocycles ranging from 22–28 atoms through spontaneous dimerization to yield bis-hydrazones

Abstract: Acid treatment of a triazine displaying both a tethered acetal and BOC-protected hydrazine group leads to spontaneous condensation to yield macrocyclic dimers in excellent yields and purity.

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Cited by 8 publications
(15 citation statements)
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References 20 publications
(18 reference statements)
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“…A folded structure for a derivative of G−G is observed using single-crystal X-ray diffraction. 25 Consistent with the prediction of a compact structure, the solid-state structure is found to be symmetric and shows extensive π−π stacking of the triazine ring upon the hydrazone. NMR obtained in CD 3 CN (Figure 2).…”
Section: ■ Results and Discussionsupporting
confidence: 76%
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“…A folded structure for a derivative of G−G is observed using single-crystal X-ray diffraction. 25 Consistent with the prediction of a compact structure, the solid-state structure is found to be symmetric and shows extensive π−π stacking of the triazine ring upon the hydrazone. NMR obtained in CD 3 CN (Figure 2).…”
Section: ■ Results and Discussionsupporting
confidence: 76%
“…The predictions from WT-MetaD simulations, both in terms of the structure and dynamic behavior of G–G , are supported by the experiments. A folded structure for a derivative of G–G is observed using single-crystal X-ray diffraction …”
Section: Resultsmentioning
confidence: 99%
“…29 Initial efforts produced macrocycles ranging from 22 to 28 atoms�each a different Murcko framework�displaying different molecular shapes ranging from ones that were compact and folded to those that were extended and flat. 27,28 During the course of these studies, however, two isomeric 24atom macrocycles were prepared�one with glycine and a three carbon acetal (−NHCH 2 CONHCH 2 CH 2 C�N−) and the other with β-alanine and a two-carbon acetal (−NHCH 2 CH 2 CONHCH 2 C�N−). 27 Both showed markedly similar, folded structures in the solid state.…”
Section: ■ Introductionmentioning
confidence: 99%
“…27,28 During the course of these studies, however, two isomeric 24atom macrocycles were prepared�one with glycine and a three carbon acetal (−NHCH 2 CONHCH 2 CH 2 C�N−) and the other with β-alanine and a two-carbon acetal (−NHCH 2 CH 2 CONHCH 2 C�N−). 27 Both showed markedly similar, folded structures in the solid state. To better define the conformational landscape associated with this framework, we chose to prepare additional 24-atom macrocycles that varied in the choice of amino acid.…”
Section: ■ Introductionmentioning
confidence: 99%
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