Synthesis of Nucleosides and Related Compounds. XXXIV. Synthesis of 5-Isonitroso-1, 3-dioxane-4, 6-diones and Their Reactions

Nobuya KATAGIRI; Hironori NOCHI; Ayumu KURIMOTO; Hiroshi SATO; Chikara KANEKO

doi:10.1248/cpb.42.1251

Synthesis of Nucleosides and Related Compounds. XXXIV. Synthesis of 5-Isonitroso-1, 3-dioxane-4, 6-diones and Their Reactions

Nobuya KATAGIRI, Hironori NOCHI, Ayumu KURIMOTO, Hiroshi SATO, Chikara KANEKO

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Keywords: 1, 3-dioxane-4, 6-dione, hydroxyiminoacetic acid, Diels-Alder reaction, asymmetric reaction, 2-azabicyclo[2.2.1]hept-5-ene, carbocyclic nucleoside

JOURNAL FREE ACCESS

1994 Volume 42 Issue 6 Pages 1251-1257

DOI https://doi.org/10.1248/cpb.42.1251

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Abstract

Synthesis of 5-isonitroso-1, 3-dioxane-4, 6-dione (2 : isonitroso Meldrum's acid) and related compounds and their reactions were described. Compound (2) reacted with various alcohols to give hydroxyiminoacetic acid esters in moderate yields. Compound 2 was acetylated in the usual manner to give 5-acetoxyimino-1, 3-dioxane-4, 6-dione (9)as a stable crystalline substance, which acted not as a heterodiene but as a heterodienophile and underwent hetero Diels-Alder reaction with various dienes to form [4+2] adducts.

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