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An efficient, large-scale synthesis of cytenamide

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Dibenzosuberenone (5H-dibenzo[a,d]cyclohepten-5-one) was reduced to the corresponding alcohol by sodium borohydride/MeOH and converted to the corresponding 5-chloro compound by thionyl chloride/benzene, treatment of which with CuCN/toluene gave the corresponding nitrile. Hydrolysis by ethanolic KOH yielded the corresponding amide, cytenamide (5H-dibenzo[a,d]cycloheptene-5-carboxamide).
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Keywords: 5H-5-CHLORODIBENZO[A,D]CYCLOHEPTENE; 5H-5-CYANODIBENZO[A,D]CYCLOHEPTENE; 5H-DIBENZO[A,D]CYCLO HEPTENE-5-CARBOXAMIDE; 5H-DIBENZO[A,D]CYCLOHEPTEN-5-ONE; CYTENAMIDE; DIBENZOSUBERENONE

Document Type: Research Article

Publication date: 01 March 2018

This article was made available online on 28 March 2018 as a Fast Track article with title: "An efficient, large-scale synthesis of cytenamide".

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  • The Journal of Chemical Research is a monthly journal which has a broad international authorship and publishes research papers and reviews in all branches of experimental chemistry.

    Established in 1977 as a joint venture by the British, French and German chemical societies it maintains the high standards set by the founding societies. Each paper is independently peer reviewed and only carefully evaluated contributions are accepted.

    Recent papers have described new synthetic methods, new heterocyclic compounds, new natural products, and the inorganic chemistry of metal complexes.

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