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Volumn 50, Issue 13, 2009, Pages 1399-1402

Convenient synthesis of heteroaryl-linked benzimidazoles via microwave-assisted boronate ester formation

Author keywords

[No Author keywords available]

Indexed keywords

BENZIMIDAZOLE DERIVATIVE; BORONIC ACID DERIVATIVE; ESTER; HALIDE;

EID: 59649120554     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.01.087     Document Type: Article
Times cited : (4)

References (20)
  • 7
    • 51549109898 scopus 로고    scopus 로고
    • For the synthesis of ester and amide substrates 1 see: (a) Hornberger, K. R.; Badiang, J. G.; Salovich, J. M.; Kuntz, K. W.; Emmitte, K. A.; Cheung, M. Tetrahedron Lett. 2008, 49, 6348. (b) Kuntz, K.; Emmitte, K. A.; Rheault, T. R.; Smith, S.; Hornberger, K.; Dickson, H.; Cheung, M. PCT Int. Appl. WO2007143456, 2007.
    • For the synthesis of ester and amide substrates 1 see: (a) Hornberger, K. R.; Badiang, J. G.; Salovich, J. M.; Kuntz, K. W.; Emmitte, K. A.; Cheung, M. Tetrahedron Lett. 2008, 49, 6348. (b) Kuntz, K.; Emmitte, K. A.; Rheault, T. R.; Smith, S.; Hornberger, K.; Dickson, H.; Cheung, M. PCT Int. Appl. WO2007143456, 2007.
  • 9
    • 59649084728 scopus 로고    scopus 로고
    • Liu, H.; Pan, W.; Xu, Y.-J. PCT Int. Appl. WO2005042496, 2005.
    • Liu, H.; Pan, W.; Xu, Y.-J. PCT Int. Appl. WO2005042496, 2005.
  • 10
    • 59649094189 scopus 로고    scopus 로고
    • For an example where the reactivity of the coupling partners is reversed see: Bonjouklian, R.; Dally, R. D.; De Dios, A.; Del Prado Catalina, M. F.; Dominguez-Fernandez, C.; Jaramillo Aguado, C.; Lopez de Uralde-Garmendia, B.; Montero Salgado, C.; Shepherd, T. A. PCT Int. Appl. WO2005080380, 2005.
    • For an example where the reactivity of the coupling partners is reversed see: Bonjouklian, R.; Dally, R. D.; De Dios, A.; Del Prado Catalina, M. F.; Dominguez-Fernandez, C.; Jaramillo Aguado, C.; Lopez de Uralde-Garmendia, B.; Montero Salgado, C.; Shepherd, T. A. PCT Int. Appl. WO2005080380, 2005.
  • 11
    • 59649101444 scopus 로고    scopus 로고
    • note
    • Ishiyama, T.; Chen, H. 4,4,4′,4′,5,5,5′,5′-Octamethyl-2,2′-bi-1,3,2-dioxaborolane. e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001.
  • 12
    • 33646497228 scopus 로고    scopus 로고
    • For examples of microwave-assisted boronate ester formation see:
    • For examples of microwave-assisted boronate ester formation see:. DiMauro E.F., and Vitullo J.R. J. Org. Chem. 71 (2006) 3959
    • (2006) J. Org. Chem. , vol.71 , pp. 3959
    • DiMauro, E.F.1    Vitullo, J.R.2
  • 16
    • 59649083529 scopus 로고    scopus 로고
    • note
    • The LC-MS data included in Table 1 were obtained using LC-MS systems calibrated on a daily basis with a system-suitability seven-component test mix to ensure fit for purpose (identity and purity).
  • 17
    • 59649102290 scopus 로고    scopus 로고
    • note
    • In addition to unreacted 1, the following by-products were also routinely observed: X = H, 2-12% by LC-MS; unreacted boronic acid, 7-11% by LC-MS; and dimers formed from homocoupling of 1, 0-6% by LC-MS.
  • 19
    • 9644262708 scopus 로고    scopus 로고
    • For examples of pyrazole and imidazole moieties functioning as Pd ligands in Suzuki-Miyaura reactions see:
    • For examples of pyrazole and imidazole moieties functioning as Pd ligands in Suzuki-Miyaura reactions see:. Mukherjee A., and Sarkar A. Tetrahedron Lett. 45 (2004) 9525
    • (2004) Tetrahedron Lett. , vol.45 , pp. 9525
    • Mukherjee, A.1    Sarkar, A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.