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Synthetic transformations of higher terpenoids: XV. Transformations of azlactone derived from 16-formyllambertianic acid methyl ester

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Abstract

Condensation of 16-formyllambertianic acid methyl ester with hippuric acid gave methyl 15,16-epoxy-16-[(4Z)-5-oxo-2-phenyl-4,5-dihydrooxazol-4-ylidenemethyl]labda-8(20),13(16),14-trien-19-oate which underwent ready transformation into 2-benzoylamino-3-(2-furyl)acrylic acid of the labdanoid series. Reactions of the diterpenoid azlactone with amines and α-amino acid esters led to the formation of the corresponding carbamoylvinylbenzamides and N-(2-benzoylaminoacryloyl) amino acid esters, and furylacrylic acid hydrazides were formed in reactions with hydrazines. Cyclization of the N′-phenylhydrazide by the action of 1 M aqueous sodium hydroxide gave the corresponding 1,2,4-triazin-6-one. By treatment of the azlactone with aqueous ammonia on heating, 4-substituted 2-phenyl-4,5-dihydroimidazol-5-one was obtained.

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Authors and Affiliations

  1. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Division, Russian Academy of Sciences, pr. Akademika Lavrent’eva 9, Novosibirsk, 630090, Russia

    Yu. V. Kharitonov, E. E. Shul’ts, M. M. Shakirov & G. A. Tolstikov

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  1. Yu. V. Kharitonov
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  2. E. E. Shul’ts
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  3. M. M. Shakirov
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  4. G. A. Tolstikov
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Original Russian Text © Yu.V. Kharitonov, E.E. Shul’ts, M.M. Shakirov, G.A. Tolstikov, 2007, published in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 6, pp. 843–854.

For communication XIV, see [1].

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Kharitonov, Y.V., Shul’ts, E.E., Shakirov, M.M. et al. Synthetic transformations of higher terpenoids: XV. Transformations of azlactone derived from 16-formyllambertianic acid methyl ester. Russ J Org Chem 43, 839–851 (2007). https://doi.org/10.1134/S1070428007060073

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  • DOI: https://doi.org/10.1134/S1070428007060073

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