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Titolo:
A MILD AND EFFICIENT METHODOLOGY FOR THE SYNTHESIS OF 5-HALOGENO URACIL NUCLEOSIDES THAT OCCURS VIA A 5-HALOGENO-6-AZIDO-5,6-DIHYDRO INTERMEDIATE
Autore:
KUMAR R; WIEBE LI; KNAUS EE;
Indirizzi:
UNIV ALBERTA,FAC PHARM & PHARMACEUT SCI EDMONTON T6G 2N8 AB CANADA UNIV ALBERTA,FAC PHARM & PHARMACEUT SCI EDMONTON T6G 2N8 AB CANADA
Titolo Testata:
Canadian journal of chemistry
fascicolo: 9, volume: 72, anno: 1994,
pagine: 2005 - 2010
SICI:
0008-4042(1994)72:9<2005:AMAEMF>2.0.ZU;2-B
Fonte:
ISI
Lingua:
ENG
Soggetto:
TUMOR UPTAKE; PYRIMIDINE; DERIVATIVES; ANALOGS; CHLORINATION; NUCLEOTIDES; C-5;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
56
Recensione:
Indirizzi per estratti:
Citazione:
R. Kumar et al., "A MILD AND EFFICIENT METHODOLOGY FOR THE SYNTHESIS OF 5-HALOGENO URACIL NUCLEOSIDES THAT OCCURS VIA A 5-HALOGENO-6-AZIDO-5,6-DIHYDRO INTERMEDIATE", Canadian journal of chemistry, 72(9), 1994, pp. 2005-2010

Abstract

A mild and efficient methodology for the synthesis of 5-halogeno (iodo, bromo, or chloro) uracil nucleosides has been developed. 5-Halo-2'-deoxyuridines 4a-c (84-95%), 5-halouridines 7a-c (45-95%), and 5-haloarabinouridines 8a-c (65-95%) were synthesized in good to excellent yields by the reaction of 2'-deoxyuridine (2), uridine (5), and arabinouridine (6), respectively, with iodine monochloride, or N-bromo (or chloro)succinimide, and sodium azide at 25-45 degrees C. These C-5 halogenation reactions proceed via a 5-halo-6-azido-5,6-dihydro intermediate (3), from which HN, is eliminated, to yield the 5-halogeno uracil nucleoside. The 5-halo-6-azido-5,6-dihydro intermediate products (10a, 10b) could be isolated from the reaction of 3',5'-di-O-acetyl-2'-deoxyuridine (9) with iodine monochloride or N-bromosuccinimide and sodium azide at 0 degrees C. The isolation of 10a, 10b indicates that the C-5 halogenation reaction proceeds via a 5-halo-6-azido-5,6-dihydro intermediate.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 25/01/21 alle ore 15:48:14