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Volumn 54, Issue 4, 2015, Pages 1190-1194

Heteroatom-embedded medium-sized cycloalkynes: Concise synthesis, structural analysis, and reactions

Author keywords

Alkynes; Cycloaddition; Heterocycles; Peptides; Strained molecules

Indexed keywords

CYCLOADDITION; HYDROCARBONS; PEPTIDES; POLYPEPTIDES; SYNTHESIS (CHEMICAL);

EID: 84920941113     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201409910     Document Type: Article
Times cited : (91)

References (70)
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    • note
    • The remaining cobalt residues in the crude reaction mixtures were easily removed by filtration through a short column of aminopropylated silica gel. See the Supporting Information.
  • 57
    • 84920965052 scopus 로고    scopus 로고
    • note
    • No reaction of 1c was observed by heating in toluene at 80°C for two weeks.
  • 58
    • 84920965051 scopus 로고    scopus 로고
    • The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif
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    • 84920965050 scopus 로고    scopus 로고
    • note
    • C-O in the transition-state geometries of the Huisgen reaction on eliminating the distortional effect of the alkyne moiety by experimental and theoretical studies, see: Ref. [12b].
  • 66
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    • note
    • C-Y in the transition state. Regarding the stereoelectronic effects of the propargylic heteroatoms on the transition state of the Huisgen reaction, a discussion by Alabugin and colleagues can be found in recent reports: Refs. [7] and [12b].
  • 67
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    • note
    • 1H NMR analysis using 1,3,5-trimethoxybenzene as an internal standard. See the Supporting Information.
  • 68
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    • note
    • No PhSH adduct of 1 f was observed in the removal of the Ns group, and strongly suggests that the bis(nitrogen)-embedded nine-membered cycloalkynes have high bioorthogonality for bioimaging technique in the presence of intravital thiols. See: Ref. [5].
  • 70
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    • note
    • The conversion of 1q and the formation of 5q in the Huisgen reaction were established by MALDI-TOF mass spectrometry with the same laser intensity and the same delay time. See the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.