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Titolo:
SYNTHESES OF [1,7-N-15(2)]- AND [1,7,NH2-N-15(3)]ADENOSINE AND 2'-DEOXYADENOSINE VIA AN N-1-ALKOXY-MEDIATED DIMROTH REARRANGEMENT
Autore:
PAGANO AR; ZHAO H; SHALLOP A; JONES RA;
Indirizzi:
RUTGERS STATE UNIV,DEPT CHEM,POB 939 PISCATAWAY NJ 08855 RUTGERS STATE UNIV,DEPT CHEM PISCATAWAY NJ 08855
Titolo Testata:
Journal of organic chemistry
fascicolo: 10, volume: 63, anno: 1998,
pagine: 3213 - 3217
SICI:
0022-3263(1998)63:10<3213:SO[A[A>2.0.ZU;2-M
Fonte:
ISI
Lingua:
ENG
Soggetto:
ACID RELATED-COMPOUNDS; NITROGEN-15-LABELED OLIGODEOXYNUCLEOTIDES; N-15 NMR; BASE-PAIR; ADENINE N1; DEOXYNUCLEOSIDES; DEOXYADENOSINE; DERIVATIVES; CONVERSION; ADENOSINE;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
35
Recensione:
Indirizzi per estratti:
Citazione:
A.R. Pagano et al., "SYNTHESES OF [1,7-N-15(2)]- AND [1,7,NH2-N-15(3)]ADENOSINE AND 2'-DEOXYADENOSINE VIA AN N-1-ALKOXY-MEDIATED DIMROTH REARRANGEMENT", Journal of organic chemistry, 63(10), 1998, pp. 3213-3217

Abstract

We have found that the N-1-methoxy derivatives of adenosine and 2'-deoxyadenosine undergo a Dimroth rearrangement in which the intermediateN,N-dimethylamino adducts are stable compounds. This mild and high-yield rearrangement allows efficient conversion of [7,NH2-N-15(2)]2'-deoxyadenosine and [7,NH2-N-15(2)]adenosine into the triply labeled [1,7,NH2-N-15(3)] derivatives. The [7,NH2-N-15(2)]nucleoside is first oxidized to the N-1-oxide with 3-chloroperoxybenzoic acid (MCPBA). Methylation of the N-1-oxide with methyl iodide or dimethyl sulfate is followed by treatment with dimethylamine to afford the 6-amino-N-1-methoxy-2-(N,N-dimethylamino) derivative. Dimroth rearrangement of these surprisingly stable intermediates is accomplished by refluxing in the presence of a dimethylammonium hydrohalide salt to give the [1,7-N-15(2)]-6-N-methoxy nucleosides in high yield. Removal of the N-6-methoxy function to afford both [1,7-N-15(2)]deoxyadenosine and [1,7-N-15(2)]adenosine was accomplished readily with Raney nickel. No hydroxyl protection is required for these transformations. Introduction of the third label at the N-6 was accomplished by conversion into the 6-(1,2,4-triazol-4-yl)purine nucleosides, followed by nucleophilic displacement of the 6-triazole with [N-15]ammonia to afford the triply labeled title compounds.

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Documento generato il 09/07/20 alle ore 19:38:02