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Volumn 2, Issue 5, 2000, Pages 475-490

5-(Hydroxymethyl)oxazoles: Versatile scaffolds for combinatorial solid-phase synthesis of 5-substituted oxazoles

Author keywords

[No Author keywords available]

Indexed keywords

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; OXAZOLE DERIVATIVE; SULFONE;

EID: 0034265122     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc0000186     Document Type: Article
Times cited : (18)

References (31)
  • 6
    • 0034723167 scopus 로고    scopus 로고
    • Report No. 512
    • Franzen, R. G. Tetrahedron 2000, 56 (Report No. 512), 685-691.
    • (2000) Tetrahedron , vol.56 , pp. 685-691
    • Franzen, R.G.1
  • 7
    • 85037507930 scopus 로고    scopus 로고
    • The booklet is provided free of charge from Chiron Technologies
    • An excellent literature review can be found in Solid-Phase Chemistry Publications. The booklet is provided free of charge from Chiron Technologies, www.chirontechnologies.com.
    • Solid-phase Chemistry Publications
  • 8
    • 85037494741 scopus 로고    scopus 로고
    • Electronic reviews and links to solid-phase organic reactions can be found at
    • Electronic reviews and links to solid-phase organic reactions can be found at www.5z.com/moldiv/.
  • 13
    • 85037517910 scopus 로고    scopus 로고
    • note
    • Alternatively, we have prepared many of the corresponding thiazoles by ring closure with 1.1 equiv Lawesson's reagent, reflux in THF, 4 h.
  • 14
    • 0029126779 scopus 로고
    • Multipins are surface functionalized graft polymers, machine shaped into gears and pins that may be mounted onto a holder. The loading details the total number of active surface sites available for reaction, e.g., a 1.6 μmole gear will theoretically produce 1.6 μmoles of product. Comprehensive details may be found at www.chirontechnologies.com. For an excellent example of parallel synthesis on multipins, see, Bastos, M.; Maeji, N. J.; Abeles, R. H. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 6738-6742.
    • (1995) Proc. Natl. Acad. Sci. U.S.A. , vol.92 , pp. 6738-6742
    • Bastos, M.1    Maeji, N.J.2    Abeles, R.H.3
  • 17
    • 0030934020 scopus 로고    scopus 로고
    • Report No. 428
    • Many reagents and conditions for deprotection of the O-allyl ether were attempted, based upon complexes of palladium, rhodium, and iridium, the chemistries of which are reviewed by Guibe, F. Tetrahedron 1997, 53 (Report No. 428), 13509-13556.
    • (1997) Tetrahedron , vol.53 , pp. 13509-13556
    • Guibe, F.1
  • 23
    • 85037506014 scopus 로고    scopus 로고
    • note
    • Early reactions were conducted on an analogue of 4{3,4} which contained the 3-phenylpropionoyl cap in place of the 3-furanoyl group. Otherwise, the sequence, gears, and loading were identical.
  • 28
    • 85037512676 scopus 로고    scopus 로고
    • note
    • The conversion of alcohol to bromide was also attempted on analogous 5-(hydroxyethyl)oxazole scaffolds. Here, the insertion of an extra methylene between the heterocycle and alcohol had a profound effect on the quality of crude molecules. The bromide was obtained in only 10-20% yield, along with two unidentified major products. Attempts to displace with azide and reduce gave a main material that was tentatively assigned as replacement of hydroxyl by DTT at m/z +138.
  • 30
    • 85037517028 scopus 로고    scopus 로고
    • note
    • Unpublished observations from an extensive examination of reaction conditions for the acylation of multipin-bound free Nα-lysine(Boc)-Rink-1.6 μmole gears with sulfonyl chlorides.
  • 31
    • 0000595570 scopus 로고    scopus 로고
    • Potential solutions to the problem of parallel quantification of combinatorial libraries are beginning to emerge, e.g., Taylor, E. W.; Qian, M. G.; Dollinger, G. D. Anal. Chem. 1998, 70, 3339-3347.
    • (1998) Anal. Chem. , vol.70 , pp. 3339-3347
    • Taylor, E.W.1    Qian, M.G.2    Dollinger, G.D.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.