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Volumn 11, Issue 15, 2013, Pages 2460-2465

Otherwise inert reaction of sulfonamides/carboxamides with formamides via proton transfer-enhanced reactivity

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION-ELIMINATION; DIFFERENT MECHANISMS; DRIVING FORCES; ENHANCED REACTIVITY; FORMAMIDES; HYDROGEN BOND INTERACTION; NON-COVALENT; TRANSFER STRATEGIES;

EID: 84877106819     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c3ob27351b     Document Type: Article
Times cited : (28)

References (54)
  • 33
    • 68949177278 scopus 로고    scopus 로고
    • Other amides like 1-formyl-piperidine and N,N-dimethylacetamide proved to be inefficient when subjected to the reaction sequences
    • S. Minakata Acc. Chem. Res. 2009 42 1172 1182
    • (2009) Acc. Chem. Res. , vol.42 , pp. 1172-1182
    • Minakata, S.1
  • 35
    • 0000582505 scopus 로고
    • ed. S. Patai and Z. Rappoport, Wiley, New York, ch. 8
    • G. V. Boyd, in The Chemistry of Amidines and Imidates, ed., S. Patai, and, Z. Rappoport, Wiley, New York, 1991, vol. 2, ch. 8
    • (1991) The Chemistry of Amidines and Imidates , vol.2
    • Boyd, G.V.1
  • 40
    • 40049108415 scopus 로고    scopus 로고
    • The efficiency of the formation of amidines and N-formylated products was relatively low. Most probably, the reversible proton transfer process is the main reason, which cannot drive the reaction to completion. Also see the mechanism part Selected examples of N-formylation, see
    • A. A. Bekhit H. M. A. Ashour Y. S. Abdel Ghany A. E.-D. A. Bekhit A. Baraka Eur. J. Med. Chem. 2008 43 456 463
    • (2008) Eur. J. Med. Chem. , vol.43 , pp. 456-463
    • Bekhit, A.A.1    Ashour, H.M.A.2    Abdel Ghany, Y.S.3    Bekhit, A.E.-D.A.4    Baraka, A.5
  • 51
    • 84858441193 scopus 로고    scopus 로고
    • Initially, we had thought it was the halogen bond interaction that activates the reaction. However, the corresponding energy barrier is too high to overcome. Hydrogen bond interaction appears to be much more reasonable based on the theoretical calculation results. For selected reviews on halogen bonding, see
    • M. I. Ansari M. K. Hussain N. Yadav P. K. Gupta K. Hajela Tetrahedron Lett. 2012 53 2063 2065
    • (2012) Tetrahedron Lett. , vol.53 , pp. 2063-2065
    • Ansari, M.I.1    Hussain, M.K.2    Yadav, N.3    Gupta, P.K.4    Hajela, K.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.