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Volumn 6, Issue 9, 2004, Pages 1405-1408

Solid-phase syntheses of furopyridine and furoquinoline systems

Author keywords

[No Author keywords available]

Indexed keywords

FUROPYRIDINE; FUROQUINOLINE; POTASSIUM CARBONATE; PYRIDINE DERIVATIVE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 2442426336     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049762f     Document Type: Article
Times cited : (38)

References (36)
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    • Furopyridine synthesis has been reviewed by: (a) Shiotani, S. Heterocycles 1997, 45, 975-1011. See also: (b) Arcadi, A.; Cacchi, S.; Di Giuseppe, S.; Fabrizi, G.; Marinelli, F. Synlett 2002, 453-457. (c) Arcadi, A.; Cacchi, S.; Di Giuseppe, S.; Fabrizi, G.; Marinelli, F. Org. Lett. 2002, 4, 2409-2412. (d) Mathes, B. M.; Filla, S. A. Tetrahedron Lett. 2003, 44, 725-728.
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    • When carried out in solution, Sonogashira cross-coupling could be accompanied by a homocoupling side reaction. For a precedent, see: (a) Siemenes, P.; Livingston, R. C.; Diederich, F. Angew. Chem., Int. Ed. 2000, 39, 2634-2657 and references therein, (b) Liao, Y.; Fathi, R.; Reitman, M.; Zhang, Y.; Yang, Z. Tetrahedron Lett. 2001, 42, 1815-1818. In the methodology of the present study, the iodophenol component is anchored on the solid phase, so homocoupled byproducts remain in solution and can be washed away.
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    • When carried out in solution, Sonogashira cross-coupling could be accompanied by a homocoupling side reaction. For a precedent, see: (a) Siemenes, P.; Livingston, R. C.; Diederich, F. Angew. Chem., Int. Ed. 2000, 39, 2634-2657 and references therein, (b) Liao, Y.; Fathi, R.; Reitman, M.; Zhang, Y.; Yang, Z. Tetrahedron Lett. 2001, 42, 1815-1818. In the methodology of the present study, the iodophenol component is anchored on the solid phase, so homocoupled byproducts remain in solution and can be washed away.
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    • note
    • Similar to ref 12, the required building blocks were made in three steps and 74-83% overall yields from commercially available 2-bromo-3-hydroxypyridine, 5-chloro-8-hydroxy-7-iodoquinoline, and o-iodoaniline. See Supporting Information for experimental details.
  • 34
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    • note
    • 1H NMR after purification (overall yields are next to the structures). Further evidence for the structures was provided by masses 106 units higher than anticipated for the desired products shown in Table 1.


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