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Volumn 63, Issue 18, 2007, Pages 3672-3681

Straightforward three-component synthesis of diarylmethylpiperazines and 1,2-diarylethylpiperazines

Author keywords

1,2 Diarylethylpiperazines; Arylzinc reagents; Benzylzinc reagents; Diarylmethylpiperazines; Three component reaction

Indexed keywords

ALDEHYDE DERIVATIVE; ETHYLPIPERAZINE DERIVATIVE; METHYLPIPERAZINE DERIVATIVE; PARAFORMALDEHYDE; PIPERAZINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 33947633056     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.02.086     Document Type: Article
Times cited : (21)

References (43)
  • 4
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    • Several patents describing functional group exchanges of diarylmethylpiperazines in biological screening purpose exist. For some recent examples, see:
  • 5
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    • Brown, W.; Griffin, A.; Penwell, A. World Patent 2006091160, 2006;
  • 6
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    • Chem. Abstr. 145 (2006) 293087
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    • Brown, W.; Griffin, A.; Hudzik, T.; Maciag, C.; Smagin, G.; Walpole, C. World Patent 2006014133, 2006;
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    • Chem. Abstr. 144 (2006) 212801
    • (2006) Chem. Abstr. , vol.144 , pp. 212801
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    • Brown, W.; Griffin, A. World Patent 2005066148, 2005;
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    • Chem. Abstr. 143 (2005) 153402
    • (2005) Chem. Abstr. , vol.143 , pp. 153402
  • 14
    • 33947642083 scopus 로고    scopus 로고
    • The displacement of benzotriazole derivatives using organometallic reagents has been first described by Katritzky. For representative examples, see:
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    • Trost B.M., and Fleming I. (Eds), Pergamon, Oxford
    • Heaney H. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 2 (1991), Pergamon, Oxford 953-973
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 953-973
    • Heaney, H.1
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    • Trost B.M., and Fleming I. (Eds), Pergamon, Oxford
    • Overman L.E., and Ricca D.J. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 2 (1991), Pergamon, Oxford 1007-1046
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 1007-1046
    • Overman, L.E.1    Ricca, D.J.2
  • 32
    • 33947671372 scopus 로고    scopus 로고
    • 1,2-Diarylethylamines are biologically active compounds. For an example in the treatment of neurotoxic injury, see: Gray, N. M.; Cheng, B. K. European Patent 346791, 1989;
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    • For more recent examples of their reuptake inhibitor activity, see:
    • Chem. Abstr. 113 (1990) 6165 For more recent examples of their reuptake inhibitor activity, see:
    • (1990) Chem. Abstr. , vol.113 , pp. 6165
  • 39
    • 0035944511 scopus 로고    scopus 로고
    • This observation is consistent with Katritzky's work, see Ref. 8e for representative examples of benzylzinc derivatives' handling. It can be noted that dialkylzinc reagents have also been employed in zirconium-catalyzed enantioselective three-component couplings, see:
    • This observation is consistent with Katritzky's work, see Ref. 8e for representative examples of benzylzinc derivatives' handling. It can be noted that dialkylzinc reagents have also been employed in zirconium-catalyzed enantioselective three-component couplings, see:. Porter J.R., Traverse J.F., Hoveyda A.H., and Snapper M.L. J. Am. Chem. Soc. 123 (2001) 10409-10410
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 10409-10410
    • Porter, J.R.1    Traverse, J.F.2    Hoveyda, A.H.3    Snapper, M.L.4
  • 40
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    • note
    • Cobalt bromide, which is used in catalytic amount during the arylzinc formation is still present in the solution when the aldehyde and the amine are added.
  • 41
    • 33947634522 scopus 로고    scopus 로고
    • note
    • Commercial solutions of phenylzinc bromide and 4-methoxyphenylzinc iodide 0.5 M in tetrahydrofuran were supplied by Aldrich.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.