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Volumn 62, Issue 49, 2006, Pages 11311-11319

New conditions for the synthesis of thiophenes via the Knoevenagel/Gewald reaction sequence. Application to the synthesis of a multitargeted kinase inhibitor

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; HEXAMETHYLDISILAZINE; PHOSPHOTRANSFERASE INHIBITOR; SILANE DERIVATIVE; TETRAHYDROFURAN; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG; WATER;

EID: 33750475937     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.07.008     Document Type: Article
Times cited : (121)

References (22)
  • 9
    • 33750484912 scopus 로고    scopus 로고
    • note
    • The addition of HMDS to AcOH is extremely exothermic and should be performed carefully. The heat of reaction is -535 J/g of HMDS. The calculated adiabatic temperature rise is 75 °C.
  • 13
    • 33750440691 scopus 로고    scopus 로고
    • note
    • 2O and added over the designated time at the designated temperature and stirring rate.
  • 15
    • 33750493202 scopus 로고    scopus 로고
    • note
    • The optimized conditions developed for 4′-nitroacetophenone (2a) were employed in these reactions, and were not further optimized for the other substrates. It is possible that these conditions do not represent the ideal process for other substrates, in particular for those with a different electronic nature (for example the 4-methoxy derivatives 2g and 3g).
  • 16
    • 33750436832 scopus 로고    scopus 로고
    • note
    • The products were isolated by crystallization. As the crystallizations were not optimized, the sometimes-large difference in assay yield and isolated yield can be attributed to high loss to the liquors.
  • 18
    • 0006912078 scopus 로고
    • and references therein
    • Freeman F., and Kim D.S.H.L. J. Org. Chem. 56 (1991) 4645-4648 and references therein
    • (1991) J. Org. Chem. , vol.56 , pp. 4645-4648
    • Freeman, F.1    Kim, D.S.H.L.2
  • 19
    • 0347579462 scopus 로고
    • For the N-alkylation of anilines by alcohols over Raney nickel, see:
    • For the N-alkylation of anilines by alcohols over Raney nickel, see:. Rice R.G., and Kohn E.J. J. Am. Chem. Soc. 77 (1955) 4052-4054
    • (1955) J. Am. Chem. Soc. , vol.77 , pp. 4052-4054
    • Rice, R.G.1    Kohn, E.J.2
  • 21
    • 33750480124 scopus 로고    scopus 로고
    • note
    • 2 of bis-acyl 12, is ruled out because overnight stirring at ambient temperature did not lower this impurity.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.