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

doi:10.1248/cpb.42.1251

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

Research output: Contribution to journal › Article › peer-review

6 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 language	English
Pages (from-to)	1251-1257
Number of pages	7
Journal	Chemical and Pharmaceutical Bulletin
Volume	42
Issue number	6
DOIs	https://doi.org/10.1248/cpb.42.1251
Publication status	Published - 1994
Externally published	Yes

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

Access to Document

10.1248/cpb.42.1251

Cite this

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

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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author = "Nobuya Katagiri and Hironori Nochi and Ayumu Kurimoto and Hiroshi Sato and Chikara Kaneko",

year = "1994",

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journal = "Chemical and Pharmaceutical Bulletin",

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publisher = "Pharmaceutical Society of Japan",

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T1 - Synthesis of Nucleosides and Related Compounds. XXXIV.1) Synthesis of 5-Isonitroso-1,3-dioxane-4,6-diones and Their Reactions

AU - Katagiri, Nobuya

AU - Nochi, Hironori

AU - Kurimoto, Ayumu

AU - Sato, Hiroshi

AU - Kaneko, Chikara

PY - 1994

Y1 - 1994

N2 - 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.

AB - 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.

KW - 1

KW - 3-dioxane-4

KW - 6-dione hydroxyiminoacetic acid Diels-Alder reaction asymmetric reaction 2-azabicy-clo[2.2.1]hept-5-ene carbocyclic nucleoside

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