Synthesis of 8',11'-dihydrospiro[cyclohexane-1,2'-oxepino[2,3- h ] chromen]-4'(3' H )-ones with ring closing metathesis as a key step

A series of novel hybrid molecular entities incorporating various spiro chromanone scaffolds onto the benzannulated oxepine core moiety were synthesised using allylation, Claisen rearrangement, Kabbe condensation and Ring Closing Metathesis (RCM) as a key step. During the synthesis we found that the...

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Published inRSC advances Vol. 8; no. 67; pp. 38673 - 38680
Main Authors K, Prathima, D, Ashok, M, Sarasija, Sripadi, Prabhakar, Vemula, Madhu, Komarraju, Venkata S, Gorai, Biswajit, Prakash, Shyam
Format Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 01.01.2018
The Royal Society of Chemistry
Subjects
Allyl compounds
Chemical reactions
Chemistry
Condensates
Cyclohexane
Metathesis
Substrates
Synthesis
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Summary:A series of novel hybrid molecular entities incorporating various spiro chromanone scaffolds onto the benzannulated oxepine core moiety were synthesised using allylation, Claisen rearrangement, Kabbe condensation and Ring Closing Metathesis (RCM) as a key step. During the synthesis we found that the nitrogen functionality in the substrate influences significantly the catalyst load due to electronic effects. Several iterations have been carried out to achieve complete conversion to products 6a-6e.
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ISSN:2046-2069
2046-2069
DOI:10.1039/c8ra07920j