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Volumn 43, Issue 46, 2002, Pages 8351-8354

Synthesis of (±)-branched-chain azaisonucleosides via Michael addition of 5-nitro-2,2-pentamethylene-1,3-dioxane to methyl 2-bromoacrylate

Author keywords

bromoacrylate; Michael reaction; Nitro compounds; Pyrrolidin 2 ones

Indexed keywords

5 NITRO 2,2 PENTAMETHYLENE 1,3 DIOXANE; ACRYLIC ACID DERIVATIVE; ALPHA BROMO GAMMA NITROESTER; DIOXANE DERIVATIVE; ESTER DERIVATIVE; METHYL 2 BROMOACRYLATE; METHYL 2,3 DIBROMOPROPANOATE; NUCLEOSIDE DERIVATIVE; PROPIONIC ACID DERIVATIVE; PYRROLIDINE DERIVATIVE; TRIETHYLAMINE; UNCLASSIFIED DRUG;

EID: 0037064532     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02012-9     Document Type: Article
Times cited : (26)

References (41)
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    • Adv. Heterocyclic Chem. , vol.68 , pp. 1-88
  • 8
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    • El Ashry, E. S. H.; El Kilany, Y. Adv. Heterocyclic Chem. 1997, 67, 391-438; 1997, 68, 1-88; 1998, 69, 129-215.
    • (1998) Adv. Heterocyclic Chem. , vol.69 , pp. 129-215
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    • 0016653046 scopus 로고
    • Kaspersen, F. M.; Pandit, U. K. J. Chem. Soc., Perkin Trans. 1 1975, 1617-1622; 1975, 1798-1802.
    • (1975) J. Chem. Soc., Perkin Trans. 1 , pp. 1798-1802
  • 22
  • 24
    • 0011101889 scopus 로고    scopus 로고
    • Compound 3 is unstable although it can be stored in the refrigerator without decomposition for 1 week.
    • Compound 3 is unstable although it can be stored in the refrigerator without decomposition for 1 week.
  • 25
    • 0011112768 scopus 로고    scopus 로고
    • 13C NMR spectra.
    • 13C NMR spectra.
  • 29
    • 0011107874 scopus 로고    scopus 로고
    • The derivatives 6 and 7 were analyzed as O,O-diacetates.
    • The derivatives 6 and 7 were analyzed as O,O-diacetates.
  • 32
    • 0011101890 scopus 로고    scopus 로고
    • The preparation of 8 appeared to be more difficult than we expected, since the bromo derivative 3 readily underwent elimination to give methyl (E)-3-(5-nitro-1,5-dioxaspiro[5.5]undec-5-yl)propenoate, e.g. treatment of 3 with sodium acetate in DMSO at room temperature afforded the O-acetyl derivative of 8 and the unsaturated nitroester in the ratio 1:1. The use of potassium trifluoroacetate decreased the amount of the elimination product to ca. 20%.
    • The preparation of 8 appeared to be more difficult than we expected, since the bromo derivative 3 readily underwent elimination to give methyl (E)-3-(5-nitro-1,5-dioxaspiro[5.5]undec-5-yl)propenoate, e.g. treatment of 3 with sodium acetate in DMSO at room temperature afforded the O-acetyl derivative of 8 and the unsaturated nitroester in the ratio 1:1. The use of potassium trifluoroacetate decreased the amount of the elimination product to ca. 20%.
  • 36
    • 0011104111 scopus 로고    scopus 로고
    • We tried to obtain derivatives 10a and 13 by reaction of the O-mesyl derivative of 9 with thymine and adenine under basic conditions in DMF, but these attempts failed; 10a was obtained in 5% yield and 13 was not isolated at all.
    • We tried to obtain derivatives 10a and 13 by reaction of the O-mesyl derivative of 9 with thymine and adenine under basic conditions in DMF, but these attempts failed; 10a was obtained in 5% yield and 13 was not isolated at all.
  • 40
    • 0011103209 scopus 로고    scopus 로고
    • Pyrrolidinol 9 was characterized as its O,N-diacetate.
    • Pyrrolidinol 9 was characterized as its O,N-diacetate.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.