Atom-efficient synthesis of 2,6-diazacyclophane compounds through alcoholysis/reduction of 3-nitroarylmethylene-2,5-piperazinediones

Readily available cyclic dehydrodipeptides are convenient starting materials for atom-efficient synthesis of different compounds. A one-pot ring-opening/alcoholysis/hydrolysis process with 3-nitroarylmethylene-2,5-piperazinediones yielded N-3-nitroarylpyruvoylamino esters, which gave the correspondi...

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Bibliographic Details
Published in:Tetrahedron 2008-03, Vol.64 (12), p.2762-2771
Main Authors: González, Juan Francisco, de la Cuesta, Elena, Avendaño, Carmen
Format: Article
Language:English
Subjects:
Azacyclophanes
Cyclic dehydrodipeptides
Indoles
Methanolysis
Peptide-like compounds
α-Ketoamides
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Summary:Readily available cyclic dehydrodipeptides are convenient starting materials for atom-efficient synthesis of different compounds. A one-pot ring-opening/alcoholysis/hydrolysis process with 3-nitroarylmethylene-2,5-piperazinediones yielded N-3-nitroarylpyruvoylamino esters, which gave the corresponding amines by reduction of the nitro group. In the case of 2-nitroaryl compounds, an intramolecular reductive amination afforded N-indole-2-carbonylamino esters, while the intermolecular reductive amination of 3- and 4-nitroaryl derivatives allowed the synthesis of 2,6-diazacyclophanes. The amino compounds may be coupled with amino acids to get peptide-like derivatives. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2008.01.047