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Volumn 16, Issue 2, 2014, Pages 536-539

Transition-metal-free synthesis of benzimidazoles mediated by KOH/DMSO

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EID: 84896767815     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol403414v     Document Type: Article
Times cited : (107)

References (48)
  • 17
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    • Benzimidazoles and Cogeneric Tricyclic Compounds For Selected Examples See: Weissberger, A., Taylor, E. C., Eds.; John Wiley & Sons: New York
    • For selected examples, see: (a) Preston, P. N. In The Chemistry of Heterocyclic Compounds; Weissberger, A., Taylor, E. C., Eds.; John Wiley & Sons: New York, 1981; Vol. 40: Benzimidazoles and Cogeneric Tricyclic Compounds p 6
    • (1981) The Chemistry of Heterocyclic Compounds , vol.40 , pp. 6
    • Preston, P.N.1
  • 34
    • 84885436884 scopus 로고    scopus 로고
    • During our studies, a potassium tert-butoxide-promoted benzimidazole synthesis starting from 2-iodoanilines and nitriles was reported
    • During our studies, a potassium tert-butoxide-promoted benzimidazole synthesis starting from 2-iodoanilines and nitriles was reported. See: Xiang, S.-K.; Tan, W.; Zhang, D.-X.; Tian, X.-L.; Feng, C.; Wang, B.-Q.; Zhao, K.-Q.; Hu, P.; Yang, H. Org. Biomol. Chem. 2013, 11, 7271.
    • (2013) Org. Biomol. Chem. , vol.11 , pp. 7271
    • Xiang, S.-K.1    Tan, W.2    Zhang, D.-X.3    Tian, X.-L.4    Feng, C.5    Wang, B.-Q.6    Zhao, K.-Q.7    Hu, P.8    Yang, H.9
  • 35
    • 0010954389 scopus 로고
    • For A Review On KOHDMSO Mixtures As "superbases
    • For a review on KOH/DMSO mixtures as "superbases", see: Trofimov, B. A. Sulfur Rep. 1992, 74, 207.
    • (1992) Sulfur Rep. , vol.74 , pp. 207
    • Trofimov, B.1
  • 36
    • 78651487650 scopus 로고    scopus 로고
    • For selected recent synthetic applications of the KOH/DMSO system
    • For selected recent synthetic applications of the KOH/DMSO system, see: (a) Cano, R.; Ramon, D. J.; Yus, M. J. Org. Chem. 2011, 76, 654
    • (2011) J. Org. Chem. , Issue.76 , pp. 654
    • Cano, R.1    Ramon, D.2    Yus, M.3
  • 39
    • 84896752932 scopus 로고    scopus 로고
    • Great Care Was Taken To Avoid The Presence Of Trace Metals In The Reaction Mixture. Those Measures Included The Transition-metal-free Synthesis Of The Starting Materials Reagent Transfers With Plastic Spatulas And The Use Of New Glassware For The Cyclization Reactions. Such Precautions Appeared Advisable In Light Of The Recent Reports On Metal Impurities Affecting Cross-coupling Reactions. For Examples See:
    • Great care was taken to avoid the presence of trace metals in the reaction mixture. Those measures included the transition-metal-free synthesis of the starting materials, reagent transfers with plastic spatulas, and the use of new glassware for the cyclization reactions. Such precautions appeared advisable in light of the recent reports on metal impurities affecting cross-coupling reactions. For examples, see:
  • 44
    • 33947449188 scopus 로고
    • For a review see
    • For a review, see: Bunnett, J. F.; Zahler, R. E. Chem. Rev. 1951, 49, 273.
    • (1951) Chem. Rev. , vol.49 , pp. 273
    • Bunnett, J.1    Zahler, R.2
  • 45
    • 84896756994 scopus 로고    scopus 로고
    • Similar observations were made in KOH/DMSO-mediated formations of benzimidazol-2-ones (ref 3a)
    • Similar observations were made in KOH/DMSO-mediated formations of benzimidazol-2-ones (ref 3a).
  • 46
    • 26644442183 scopus 로고
    • For nucleophilic substitution reactions involving electron transfer
    • For nucleophilic substitution reactions involving electron transfer, see: (a) Bunnett, J. F. Acc. Chem. Res. 1978, 11, 413.
    • (1978) Acc. Chem. Res. , vol.11 , pp. 413
    • Bunnett, J.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.