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Volumn 68, Issue 17, 2003, Pages 6788-6790

5-Endo-dig electrophilic cyclization of α-alkynyl carbonyl compounds: Synthesis of novel bicyclic 5-iodo- and 5-bromofuranopyrimidine nucleosides

Author keywords

[No Author keywords available]

Indexed keywords

ELECTROPHILIC CYCLIZATION;

EID: 0042009107     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0345648     Document Type: Article
Times cited : (65)

References (61)
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    • Conversion of alkynyl uridines to 5-aryl substituted furano pyrimidines has been reported: Carangio, A.; McGuigan, C.; Andrei, G.; Snoeck, R.; De Clercq, E.; Balzarini, J. Antiviral Chem. Chemother. 2001, 12, 187-197. Also carbonylative annulation allows for functionalization of benzofurans at analogous position: Liao, Y.; Reitman, M.; Zhang, Y.; Fathi, R.; Yang, Z. Org. Lett. 2002, 4, 2607-2609. Chaplin, J. H.; Flynn, B. L. Chem. Commun. 2001, 1594-1595.
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    • note
    • In a preliminary studies, the iodonucleoside 3a was tested using cytotoxicity assay and exhibited activity comparable to 5-fluorouracil. We are indebt to Prof. Rasul Chaudry for this experiment.
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    • note
    • 4C≡CH in Sonogashira conditions. We thank Ms. Bo Bezeau for this observation.
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