메뉴 건너뛰기




Volumn 48, Issue 11, 2007, Pages 1983-1986

Conformationally restricted 4-dimethylaminopyridine (DMAP) analogs: synthesis and evaluation of catalytic effectiveness

Author keywords

4 Dimethylaminopyridine; Acylation of alcohols; Cyclization; Nucleophilic catalysis; Sonogashira reaction

Indexed keywords

4 DIMETHYLAMINOPYRIDINE; ALCOHOL DERIVATIVE;

EID: 33846920817     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.01.066     Document Type: Article
Times cited : (27)

References (46)
  • 12
    • 0000784289 scopus 로고    scopus 로고
    • and references cited therein
    • Ragnarsson U., and Grehn L. Acc. Chem. Res. 31 (1998) 494-501 and references cited therein
    • (1998) Acc. Chem. Res. , vol.31 , pp. 494-501
    • Ragnarsson, U.1    Grehn, L.2
  • 31
    • 33746797651 scopus 로고    scopus 로고
    • The reaction scheme presented is strictly correct only for sterically unhindered acyl donors, where the catalytic route is considerably faster than the uncatalyzed reaction
    • Fischer C.B., Xu S., and Zipse H. Chem. Eur. J. 12 (2006) 5779-5784 The reaction scheme presented is strictly correct only for sterically unhindered acyl donors, where the catalytic route is considerably faster than the uncatalyzed reaction
    • (2006) Chem. Eur. J. , vol.12 , pp. 5779-5784
    • Fischer, C.B.1    Xu, S.2    Zipse, H.3
  • 32
    • 4243664295 scopus 로고
    • m(Alkyl) = -0.06
    • m(Alkyl) = -0.06. Hansch C., and Taft R.W. Chem. Rev. 91 (1991) 165-195
    • (1991) Chem. Rev. , vol.91 , pp. 165-195
    • Hansch, C.1    Taft, R.W.2
  • 33
    • 8444241193 scopus 로고    scopus 로고
    • The acylpyridinium salt derived from DMAP has a higher solubility than that from pyridine, and this could also contribute to its greater effectiveness
    • The acylpyridinium salt derived from DMAP has a higher solubility than that from pyridine, and this could also contribute to its greater effectiveness. Spivey A.C., and Arseniyadis S. Angew. Chem., Int. Ed. 43 (2004) 5436-5441
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 5436-5441
    • Spivey, A.C.1    Arseniyadis, S.2
  • 35
    • 33846895527 scopus 로고    scopus 로고
    • Pascal, R. A. Jr., Personal communication. DFT calculations for 3 were performed by using gaussian-98; the built-in default thresholds for wavefunction and gradient convergence were employed. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, M. R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Salvador, P.; Dannenberg, J. J.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G. A.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. gaussian-98 (Revision A. 7), Gaussian, Pittsburgh, PA, 2001.
  • 37
    • 33846915546 scopus 로고    scopus 로고
    • note
    • While 4-N lone pair orbital parallel to the π system is beneficial for the first step, it is partially detrimental for the second step because it makes N-C{double bond, long}O bond breaking difficult, and so it is conceivable that some flexibility in the ring system might be beneficial for catalysis.
  • 46
    • 33846924132 scopus 로고    scopus 로고
    • note
    • 3OD) δ: 157.39, 148.73, 129.37, 52.17, 30.61, 26.95, 25.29.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.