Synthesis of Nucleosides and Related Compounds. XXXIV.1) 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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11 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)1251-1257
Number of pages7
JournalChemical and Pharmaceutical Bulletin
Volume42
Issue number6
DOIs
Publication statusPublished - 1994

Keywords

  • 1
  • 3-dioxane-4
  • 6-dione hydroxyiminoacetic acid Diels-Alder reaction asymmetric reaction 2-azabicy-clo[2.2.1]hept-5-ene carbocyclic nucleoside

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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