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Volumn 49, Issue 36, 2008, Pages 5332-5335

POCl3-mediated synthesis of hydrolysis-prone 2-trifluoroethylbenzimidazoles

Author keywords

2 Trifluoroethylbenzimidazole; Trifluoromethyl hydrolysis

Indexed keywords

2 TRIFLUOROETHYLBENZIMIDAZOLE DERIVATIVE; BENZIMIDAZOLE DERIVATIVE; PHOSPHORUS CHLORIDE OXIDE; PHOSPHORUS PENTOXIDE;

EID: 47549090593     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.06.069     Document Type: Article
Times cited : (4)

References (24)
  • 5
    • 47549091563 scopus 로고    scopus 로고
    • Ng, R.; Sui, Z.; Guan, J.; Lanter, J. C.; Alford, V. C., Jr. Novel Benzimidazole Derivatives Useful As Selective Androgen Receptor Modulators (SARMS). WO 2006/039243 A1, 2006.
    • Ng, R.; Sui, Z.; Guan, J.; Lanter, J. C.; Alford, V. C., Jr. Novel Benzimidazole Derivatives Useful As Selective Androgen Receptor Modulators (SARMS). WO 2006/039243 A1, 2006.
  • 6
    • 47549100620 scopus 로고    scopus 로고
    • Liu, Z.; Milburn, C.; Page, D.; Walpole, C.; Yang, H. Benzimidazole Derivatives, Compositions Containing Them, Preparation Thereof And Uses Thereof. WO 2005/030762 A1, 2006.
    • Liu, Z.; Milburn, C.; Page, D.; Walpole, C.; Yang, H. Benzimidazole Derivatives, Compositions Containing Them, Preparation Thereof And Uses Thereof. WO 2005/030762 A1, 2006.
  • 7
    • 47549097205 scopus 로고    scopus 로고
    • Anderskewitz, R.; Martyres, D.; Dollinger, H.; Pouzet, P.; Birke, F.; Bouyssou, T. Haloalkyl- and Piperidine-Substituted Benzimidazole-Derivatives. WO 2005/019203 A1, 2005.
    • Anderskewitz, R.; Martyres, D.; Dollinger, H.; Pouzet, P.; Birke, F.; Bouyssou, T. Haloalkyl- and Piperidine-Substituted Benzimidazole-Derivatives. WO 2005/019203 A1, 2005.
  • 9
    • 47549115642 scopus 로고
    • 3 has not been previously employed in the synthesis of 2-trifluoroethylbenzimidazoles, this reagent has been successfully used to prepare non-fluorinated benzimidazoles by cyclodehydration. For example:
    • 3 has not been previously employed in the synthesis of 2-trifluoroethylbenzimidazoles, this reagent has been successfully used to prepare non-fluorinated benzimidazoles by cyclodehydration. For example:. Kurasawa Y., Shimabukuro S., Okamoto Y., and Takeda A. Heterocycles 23 (1985) 65
    • (1985) Heterocycles , vol.23 , pp. 65
    • Kurasawa, Y.1    Shimabukuro, S.2    Okamoto, Y.3    Takeda, A.4
  • 19
    • 47549104125 scopus 로고    scopus 로고
    • note
    • Consistent with this is our observation that compound 11, which cannot eliminate HF, converts cleanly to 12 under acidic conditions. No evidence for loss of the trifluoromethyl group was observed {A figure is presented}.
  • 20
    • 0001385309 scopus 로고
    • Hydrolysis of perfluorinated alkenes has been observed under acidic and basic conditions. For example:
    • Hydrolysis of perfluorinated alkenes has been observed under acidic and basic conditions. For example:. England D.C. J. Org. Chem. 46 (1981) 147
    • (1981) J. Org. Chem. , vol.46 , pp. 147
    • England, D.C.1
  • 22
    • 0038754759 scopus 로고    scopus 로고
    • Protonation of the benzimidazole nitrogen is likely under acidic conditions and may favor the decarboxylation event. Consistent with this, indole-2-acetic acids are stable and can be prepared by hydrolysis of the corresponding esters. For example:
    • Protonation of the benzimidazole nitrogen is likely under acidic conditions and may favor the decarboxylation event. Consistent with this, indole-2-acetic acids are stable and can be prepared by hydrolysis of the corresponding esters. For example:. Weber D., Berger C., Eickelmann P., Antel J., and Kessler H. J. Med. Chem. 46 (2003) 1918
    • (2003) J. Med. Chem. , vol.46 , pp. 1918
    • Weber, D.1    Berger, C.2    Eickelmann, P.3    Antel, J.4    Kessler, H.5
  • 24
    • 47549103943 scopus 로고    scopus 로고
    • note
    • All 2-trifluoroethylbenzimidazoles listed in Table 2 are transformed to the corresponding 2-methylbenzimidazoles when heated in AcOH at 100 °C (observed by LC/MS).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.