Novel cinnamic acid analogues: synthesis of aminotroponyl acrylates by Pd()-catalysed C(sp)-H olefination

Cinnamic acid, a benzenoid scaffold, is a building block of various natural products. This report describes the synthesis of new non-benzenoid cinnamate analogs, 3-(6-amino-7-oxocyclohepta-1,3,5-trien-1-yl)acrylates, obtained through Pd( ii )-catalyzed C7-H olefination of 2-aminotropones in the pres...

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Bibliographic Details
Published inChemical communications (Cambridge, England) Vol. 58; no. 58; pp. 877 - 88
Main Authors Jena, Chinmay K, Sharma, Nagendra K
Format Journal Article
LanguageEnglish
Published Cambridge Royal Society of Chemistry 19.07.2022
Subjects
Acrylates
Analogs
Carbonyls
Cinnamic acid
Couplings
Natural products
Peptides
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Summary:Cinnamic acid, a benzenoid scaffold, is a building block of various natural products. This report describes the synthesis of new non-benzenoid cinnamate analogs, 3-(6-amino-7-oxocyclohepta-1,3,5-trien-1-yl)acrylates, obtained through Pd( ii )-catalyzed C7-H olefination of 2-aminotropones in the presence of acrylates. In these site-selective couplings, the troponyl-carbonyl function acts as a directing group. This strategy has been employed for the synthesis of new pseudopeptides from prolyl/prolamide containing aminotropone derivatives. These novel troponyl cinnamate analogs are potential precursors of hairpin forming peptides. Cinnamic acid, a benzenoid scaffold, is a building block of various natural products.
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For ESI and crystallographic data in CIF or other electronic format see DOI
13
2145592
Electronic supplementary information (ESI) available
H/
https://doi.org/10.1039/d2cc02276a
C NMR and HRMS spectra of new synthetic compounds, and single crystal X-ray parameters of pseudopeptides are also provided. CCDC
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ISSN:1359-7345
1364-548X
DOI:10.1039/d2cc02276a