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Volumn 79, Issue 20, 2014, Pages 9754-9761

1-oxo-1H-phenalene-2,3-dicarbonitrile heteroaromatic scaffold: Revised structure and mechanistic studies

Author keywords

[No Author keywords available]

Indexed keywords

MECHANISTIC STUDIES;

EID: 84908243274     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo5016932     Document Type: Article
Times cited : (18)

References (50)
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    • Chen, Z.; et al. J. Med. Chem. 2014, 57, 1621-1624;
    • (2014) J. Med. Chem. , vol.57 , pp. 1621-1624
    • Chen, Z.1
  • 2
    • 84904989205 scopus 로고    scopus 로고
    • Chem. Commun. 2014, 50, 9596-9598;
    • (2014) Chem. Commun. , vol.50 , pp. 9596-9598
  • 3
    • 84889237346 scopus 로고    scopus 로고
    • and cited literature therein
    • Song, T.; et al. J. Med. Chem. 2013, 56, 9366-9367 and cited literature therein.
    • (2013) J. Med. Chem. , vol.56 , pp. 9366-9367
    • Song, T.1
  • 33
    • 0000248247 scopus 로고
    • (a) Jones, G. Org. React. 1967, 15, 204-599.
    • (1967) Org. React. , vol.15 , pp. 204-599
    • Jones, G.1
  • 39
    • 84908257306 scopus 로고    scopus 로고
    • note
    • 1H NMR, COSY, and HSQC spectra are disclosed in the Supporting Information.
  • 40
    • 84908233892 scopus 로고    scopus 로고
    • note
    • NAr-H on the aromatic moiety. The experimental procedure and analytical data are described in the Experimental Section. For further details of structure elucidation (X-Ray and HMBC experiments), see the Supporting Information.
  • 41
    • 84908251054 scopus 로고    scopus 로고
    • note
    • H with any nucleophile.
  • 43
    • 84908223212 scopus 로고    scopus 로고
    • note
    • These chemical yields are not representative to the global yield of the reaction. It is reasonable to consider a global yield that is much higher than around 40% since two dainty purifications on silica gel were needed to isolate both compounds 12 and 13 as pure materials for fine structural analysis.
  • 44
    • 84908253158 scopus 로고    scopus 로고
    • note
    • The mentioned chemical yields are related to the amount of compounds collected as pure material to complete fine structural analysis.
  • 45
    • 84908230767 scopus 로고    scopus 로고
    • note
    • The same experiment was carried out in presence of N-methylmorpholine oxide (1.2 equiv) and gave the same compounds in a different ratio. Both pure regiosisomers 12 and 13 were isolated in similar yields, 15 and 16%, respectively. Once again, compound 14 was also obtained in 6% yield. For more details about oxidative nucleophilic hydrogen substitution (using an oxidant such as N-methylmorpholine N-oxide), see ref 8.
  • 47
    • 84908255570 scopus 로고    scopus 로고
    • note
    • The same experiment was carried out under classical thermic conditions (7.5 h at 60°C) and gave rise to compound 18 in 21% yield (isolated as pure compound).
  • 49
    • 84908250173 scopus 로고    scopus 로고
    • note
    • For confirmation of this structural assignment, see the X-ray section of the Supporting Information.
  • 50
    • 84908238782 scopus 로고    scopus 로고
    • note
    • 2).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.