A Silicon Linker for Direct Loading of Aromatic Compounds to Supports. Traceless Synthesis of Pyridine-Based Tricyclics

Journal of Organic Chemistry

Volumn 62, Issue 18, 1997, Pages 6102-6103

  Woolard, Frank X ^a,b   Paetsch, Jonathan ^a   Ellman, Jonathan A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b Zeneca Ag Products   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001655885     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9710745     Document Type: Article

References (20)

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5. (d) Plunkett, M. J.; Ellman, J. A. J. Org. Chem, 1997, 62, 2885.
6. For a recent review on linkage strategies and methods see: Backes, B. J.; Ellman, J. A. Curr. Opin. Chem. Biol. 1997, 1, 86.
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13. The loading efficiency of 2 ranges from 85-95% based upon the bromine substitution level of the starting resin.
14. Prepared in three steps from commercially available 2-amino-5-bromo-3-nitropyridine (see Supporting Information).
15. Boojamra, C. G.; Burow, K. M.; Ellman, J. A. J. Org. Chem. 1995, 60, 5742.
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18. 2-Chloro-substituted oxazolidines previously have been reported in the literature. (a) Falck, J. R.; Manna, S.; Mioskowski, C. J. Org. Chem. 1981, 46, 3742. (b) Larsen, R. D.; Reamer, R. A.; Corley, E. G.; Davis, P.; Grabowski, E. J. J.; Reider, P. J.; Shinkai, I. J. Org, Chem. 1991, 56, 6034.
19. 2-Chloro-substituted oxazolidines previously have been reported in the literature. (a) Falck, J. R.; Manna, S.; Mioskowski, C. J. Org. Chem. 1981, 46, 3742. (b) Larsen, R. D.; Reamer, R. A.; Corley, E. G.; Davis, P.; Grabowski, E. J. J.; Reider, P. J.; Shinkai, I. J. Org, Chem. 1991, 56, 6034.
20. 4NF. The corresponding solution-phase azide reduction also provides 2-chlorooxazolidine intermediates.