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Iminofuran chemistry: VII. Intramolecular cyclization of 2-N-aryl-substituted derivatives of 2-amino-4-aryl-4-oxobut-2-enoic and 2-amino-5,5-dimethyl4-oxohex-2-enoic acids

Research paper by A. V. Tyuneva, N. M. Igidov, N. N. Koryagina, A. Yu. Borodin, A. V. Zakhmatov, A. S. Makarov, Yu. C. Toksarova, A. E. Rubtsov

Indexed on: 10 Mar '11Published on: 10 Mar '11Published in: Russian Journal of Organic Chemistry



Abstract

The cyclization at the treatment of acetic anhydride of 4-aryl-2-arylamino-4-oxobut-2-enoic and 2-arylamino-5,5-dimethyl-4-oxohex-2-enoic acids was investigated furnishing derivatives of 5-aryl-3-aryl-imino-3H-furan-2-ones and 4-arylamino-2-tert-butyl-2,5-dihydro-5-oxofuran-2-yl acetate respectively. 2-N2-Methylenesubstituted 4-aryl-2-hydrazino-4-oxobut-2-enoic and 5,5-dimethyl-2-hydrazino-4-oxohex-2-enoic acids cleanly underwent cyclization under the effect of acetic anhydride into 5-aryl-3-hydrazono-3H-furan-2-ones and 5-tert-butyl-3-hydrazono-3H-furan-2-ones.