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Volumn 38, Issue 8, 1999, Pages 1073-1077

An oxidation-labile traceless linker for solid-phase synthesis

Author keywords

Antibiotics; Combinatorial chemistry; Hydrazides; Oxidations; Solid phase synthesis

Indexed keywords

ANTIBIOTIC AGENT; HYDRAZIDE; TRIAZENE DERIVATIVE;

EID: 0033583545     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19990419)38:8<1073::AID-ANIE1073>3.0.CO;2-Y     Document Type: Article
Times cited : (89)

References (42)
  • 17
    • 33745173087 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 1998, 37, 3413-3415;
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 3413-3415
  • 23
    • 33747569561 scopus 로고    scopus 로고
    • note
    • Notably, the cleavage of molecules from solid supports by cyclization reactions (e. g. by ring-closing metathesis or amide bond formation) also provides opportunities for utilizing traceless linkers, albeit usually not by the formation of C-H bonds. See references [1] and [2o] for examples and further discussion.
  • 26
    • 0032563916 scopus 로고    scopus 로고
    • b) C. R. Millington, R. Quarrell, G. Lowe, Tetrahedron Lett. 1998, 39, 7201-7204. These authors also noted and proposed that aryl hydrazides might be used as traceless linker for aromatic hydrocarbons. However, corresponding experiments were not reported. When this paper appeared the basic methodology described here had already been developed independently in our laboratory.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 7201-7204
    • Millington, C.R.1    Quarrell, R.2    Lowe, G.3
  • 27
    • 33747537691 scopus 로고    scopus 로고
    • note
    • -1.
  • 32
    • 33747551785 scopus 로고    scopus 로고
    • note
    • II does not oxidize the hydrazides to the acyl diazenes.
  • 33
    • 33747527687 scopus 로고    scopus 로고
    • note
    • In the oxidation bromide ions are formed. The finding that the acyl diazenes remain polymer-bound shows that the nucleophilicity of Br-is not sufficient to cleave the oxidized linker.
  • 34
    • 33747562216 scopus 로고    scopus 로고
    • note
    • The corresponding vinyl bromide resulting from hydrobromination of the triple bond was isolated as a side product.
  • 35
    • 33747579969 scopus 로고    scopus 로고
    • note
    • 2/HCl).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.