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Volumn 6, Issue 12, 2004, Pages 2019-2022

Microwave-Accelerated SPOT-synthesis on cellulose supports

Author keywords

[No Author keywords available]

Indexed keywords

CELLULOSE;

EID: 3042708379     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049313f     Document Type: Article
Times cited : (72)

References (32)
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    • (2000) Science , vol.287 , pp. 1964-1969
    • Schreiber, S.L.1
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    • 0141512514 scopus 로고    scopus 로고
    • For recent commentaries on microwave-assisted combinatorial chemistry, see: (a) Blackwell, H. E. Org. Biomol. Chem. 2003, 1, 1251-1255. (b) Kappe, C. O. Curr. Opin. Chem. Biol. 2002, 6, 314-320.
    • (2003) Org. Biomol. Chem. , vol.1 , pp. 1251-1255
    • Blackwell, H.E.1
  • 10
    • 0036603599 scopus 로고    scopus 로고
    • For recent commentaries on microwave-assisted combinatorial chemistry, see: (a) Blackwell, H. E. Org. Biomol. Chem. 2003, 1, 1251-1255. (b) Kappe, C. O. Curr. Opin. Chem. Biol. 2002, 6, 314-320.
    • (2002) Curr. Opin. Chem. Biol. , vol.6 , pp. 314-320
    • Kappe, C.O.1
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    • 0026656122 scopus 로고
    • Frank, R. Tetrahedron 1992, 48, 9217-9232.
    • (1992) Tetrahedron , vol.48 , pp. 9217-9232
    • Frank, R.1
  • 12
    • 0036721834 scopus 로고    scopus 로고
    • For a recent SPOT-synthesis review, see: Frank, R. J. Immunol. Methods 2002, 267, 13-26.
    • (2002) J. Immunol. Methods , vol.267 , pp. 13-26
    • Frank, R.1
  • 13
    • 85039514251 scopus 로고    scopus 로고
    • note
    • 2).
  • 14
    • 0035951563 scopus 로고    scopus 로고
    • For selected examples, see: (a) Scharn, D.; Germeroth, L.; Schneider-Mergener, J.; Wenschuh, H. J. Org. Chem. 2001, 66, 507-513. (b) Jobron, L.; Hummel, G. Angew. Chem., Int. Ed. 2000, 39, 1621-1624. Ast, T.; Heine, N.; Germeroth, L.; Schneider-Mergener, J.; Wenschuh, H. Tetrahedron Lett. 1999, 40, 4317-4318.
    • (2001) J. Org. Chem. , vol.66 , pp. 507-513
    • Scharn, D.1    Germeroth, L.2    Schneider-Mergener, J.3    Wenschuh, H.4
  • 15
    • 0034595341 scopus 로고    scopus 로고
    • For selected examples, see: (a) Scharn, D.; Germeroth, L.; Schneider-Mergener, J.; Wenschuh, H. J. Org. Chem. 2001, 66, 507-513. (b) Jobron, L.; Hummel, G. Angew. Chem., Int. Ed. 2000, 39, 1621-1624. Ast, T.; Heine, N.; Germeroth, L.; Schneider-Mergener, J.; Wenschuh, H. Tetrahedron Lett. 1999, 40, 4317-4318.
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 1621-1624
    • Jobron, L.1    Hummel, G.2
  • 16
    • 0033522834 scopus 로고    scopus 로고
    • For selected examples, see: (a) Scharn, D.; Germeroth, L.; Schneider-Mergener, J.; Wenschuh, H. J. Org. Chem. 2001, 66, 507-513. (b) Jobron, L.; Hummel, G. Angew. Chem., Int. Ed. 2000, 39, 1621-1624. (c) Ast, T.; Heine, N.; Germeroth, L.; Schneider-Mergener, J.; Wenschuh, H. Tetrahedron Lett. 1999, 40, 4317-4318.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 4317-4318
    • Ast, T.1    Heine, N.2    Germeroth, L.3    Schneider-Mergener, J.4    Wenschuh, H.5
  • 24
    • 85039514936 scopus 로고    scopus 로고
    • note
    • Functionalization levels were determined by quantitation of Fmoc-derivatized amino-support 3 using UV spectroscopy (at 296 nm).
  • 25
    • 85039523828 scopus 로고    scopus 로고
    • note
    • All MW-assisted reactions on cellulose supports were performed in a Milestone Ethos Microsynth multimodal reactor using power (wattage) control. Temperature control was not possible due to the low solvent volumes used. Supports were washed with various solvents and dried routinely between each synthesis step; see the Supporting Information.
  • 27
    • 85039538103 scopus 로고    scopus 로고
    • note
    • Compounds were cleaved quantitatively from the Wang linker by treatment with TFA vapor (in a vacuum desiccator, 25°C, 60 min). See refs 11 and 19.
  • 28
    • 85039521244 scopus 로고    scopus 로고
    • note
    • Both cis and trans chalcone isomers were observed in certain cases; see the Supporting Information.
  • 29
    • 85039541218 scopus 로고    scopus 로고
    • note
    • Control SPOT reactions (30 min, 25°C) generated chalcones in low yields (ca. 10%); see the Supporting Information.
  • 30
    • 0008143556 scopus 로고
    • The absolute tautomeric form of 13 remains unknown. Dihydropyrimidines can exist as 1,4 or 1,6 annular tautomers, see: Weis, A. L. Tetrahedron Lett. 1982, 23, 449-452.
    • (1982) Tetrahedron Lett. , vol.23 , pp. 449-452
    • Weis, A.L.1
  • 31
    • 85039521079 scopus 로고    scopus 로고
    • note
    • Perloza MT-100 is commercially available from Iontosorb Co.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.