II. C-nucleosides and related compounds carbocyclic analogues of C-nucleosides: A useful intermediate

Just, George; Reader, G.

doi:10.1016/s0040-4039(01)95987-8

Cited by 12 publications

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References 12 publications

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“…Cyclization with sodium following manner. Olefinic ester 18 (6) was methoxide in methanol gave the cyclized product oxidized with potassium permanganate and 11 in 30% yield. Pure anti-isomer 8-E was sodium periodate (7 reduced with diborane to give 22.…”

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C-Nucleosides and related compounds. XII. The synthesis of the carbocyclic analogues of D, L-6-azapseudouridine, 2-thio-6-azapseu douridine, and pyrazofurin A. On the cyclization of semicarbazones of α-keto esters

Just¹,

Kim²

1977

Can. J. Chem.

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GEORGE JUST and SUNGGAK KIM. Can. J. Chem. 55, 427 (1977). The preparation of the title compounds is described. The cycli~ation of the syn-and antiisomers of semicarbazones, thiosemicarbazones, and carbomethoxymethyl hydrazones to azauracils, thioazauracils, and pyrazoles is described. The photochemical isomerization of the hydrazones has been carried out. Whereas both syn-and anti-isomers of the thiosemicarbazones and carbomethoxymethyl hydrazones cyclize, only the syrz-isomer of the semicarbazones can be converted to the corresponding azauracil.GEORGE JUST et SUNGGAK KIM. Can. J. Chem. 55, 427 (1977) On decrit la preparation des composes mentionnes dans le titre. On decrit la cyclisation des isomeres syn et anti des semicarbazones, des thiosemicarbazones et des carbomethoxymtthyles hydrazones en azauracils, thioazauracils et pyrazoles. On a effectut les isomCrisations photochimiques des hydrazones. Alors que les isomeres syn ainsi que anti des thiosemicarbazones et carbomethoxymCthyles hydrazones peuvent se cycliser, il n'y a que l'isomere syn des semicarbazones qui peut &tre transform6 en azauracil correspondant.[Traduit par le journal]In the course of the synthesis of the carbocyclic analogue of D,L-pyrazofurin A 17 (I), it was noted that the cyclization of the corresponding hydrazone 10 proceeded in low yield, and that the hydrazone consisted of a mixture of the synand anti-isomers. It occurred to us that perhaps only one isomer underwent cyclization.The cyclization behaviour of semicarbazones is also a somewhat capricious reaction. It has of pyruvic acid underwent a high yield cyclization resulting in the formation of 6. Replacement of the sulfur atom with an oxygen atom then allowed him to prepare 6-azathymine 4 (5). In contrast with the cyclization of semicarbazones of a-keto acids, the cyclization of thiosemicarbazones proceeds consistently in good yield.

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C-Nucleosides and related compounds. XII. The synthesis of the carbocyclic analogues of D, L-6-azapseudouridine, 2-thio-6-azapseu douridine, and pyrazofurin A. On the cyclization of semicarbazones of α-keto esters

Just¹,

Kim²

1977

Can. J. Chem.

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“…The known Diels-Alder adduct (3) between cyclopentadiene and (E)-P-bromoacrylic acid was esterified to give ester 1 (4). Hydroboration of ester 1, followed by oxidation with alkaline hydrogen peroxide, gave two compounds in a ratio of 57:43.…”

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C-Nucleosides and related compounds. XI. The synthesis of the 2-deoxy carbocyclic analogue of D,L-pyrazofurin A

Just¹,

Kim²

1976

Can. J. Chem.

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ChemInform Abstract: 2. MITT. C‐NUCLEOSIDE UND VERWANDTE VERBINDUNGEN , CARBOCYCLISCHE ANALOGA VON C‐NUCLEOSIDEN, EINE NUETZLICHE ZWISCHENSTUFE

Just¹,

Reader²

1973

Chemischer Informationsdienst

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II. C-nucleosides and related compounds carbocyclic analogues of C-nucleosides: A useful intermediate

Cited by 12 publications

References 12 publications

C-Nucleosides and related compounds. XII. The synthesis of the carbocyclic analogues of D, L-6-azapseudouridine, 2-thio-6-azapseu douridine, and pyrazofurin A. On the cyclization of semicarbazones of α-keto esters

C-Nucleosides and related compounds. XII. The synthesis of the carbocyclic analogues of D, L-6-azapseudouridine, 2-thio-6-azapseu douridine, and pyrazofurin A. On the cyclization of semicarbazones of α-keto esters

C-Nucleosides and related compounds. XI. The synthesis of the 2-deoxy carbocyclic analogue of D,L-pyrazofurin A

ChemInform Abstract: 2. MITT. C‐NUCLEOSIDE UND VERWANDTE VERBINDUNGEN , CARBOCYCLISCHE ANALOGA VON C‐NUCLEOSIDEN, EINE NUETZLICHE ZWISCHENSTUFE

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