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Volumn 45, Issue 19, 2004, Pages 3725-3728

Expeditive synthesis of homochiral fused tri- and tetrazoles-piperazines from β-amino alcohols

Author keywords

Organolithium; Tetrazoles; Triazoles

Indexed keywords

4,5,6,7 TETRAHYDRO[1,2,3]TRIAZOLO[1,5 A]PYRAZINE; 5,6,7,8 TETRAHYDROTETRAZOLO[1,5 A]PYRAZINE; ALCOHOL DERIVATIVE; AMINOALCOHOL; BETA AMINO ACID; DIMETHYL SULFOXIDE; PIPERAZINE DERIVATIVE; PYRAZINE DERIVATIVE; TETRAZOLE DERIVATIVE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 1842828947     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.03.092     Document Type: Article
Times cited : (50)

References (19)
  • 7
    • 0034605815 scopus 로고    scopus 로고
    • For a recent example of synthesis of fused tetrazole-ketopiperazines, see:
    • For a recent example of synthesis of fused tetrazole-ketopiperazines, see: Nixey T., Kelly M., Hulme C. Tetrahedron Lett. 41:2000;8729-8733.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 8729-8733
    • Nixey, T.1    Kelly, M.2    Hulme, C.3
  • 8
    • 0242576129 scopus 로고    scopus 로고
    • For a recent theoretical study, see:
    • For a recent theoretical study, see: Himo F., Demko Z.P., Noodleman L. J. Org. Chem. 68:2003;9076-9080.
    • (2003) J. Org. Chem. , vol.68 , pp. 9076-9080
    • Himo, F.1    Demko, Z.P.2    Noodleman, L.3
  • 9
  • 13
    • 1842857950 scopus 로고    scopus 로고
    • note
    • This may be ascribed to an nN → σ *C-CN overlap (anomeric effect), which deactivates the lone pair on the nitrogen in N-cyanomethyl derivatives.
  • 16
    • 0742304467 scopus 로고    scopus 로고
    • For a recent example reporting the lithiation α to the carbon of a tetrazole heterocycle, see:
    • For a recent example reporting the lithiation α to the carbon of a tetrazole heterocycle, see: Yang M.G., Modi D.P., Wexler R.R., Olson R.E. Tetrahedron Lett. 45:2004;111-112.
    • (2004) Tetrahedron Lett. , vol.45 , pp. 111-112
    • Yang, M.G.1    Modi, D.P.2    Wexler, R.R.3    Olson, R.E.4
  • 17
    • 0031033075 scopus 로고    scopus 로고
    • N-Boc α-lithio piperazines are known to undergo β-elimination:
    • N-Boc α-lithio piperazines are known to undergo β-elimination: Garrido F., Mann A., Wermuth C.-G. Tetrahedron Lett. 38:1997;63-64.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 63-64
    • Garrido, F.1    Mann, A.2    Wermuth, C.-G.3
  • 19
    • 9444267537 scopus 로고    scopus 로고
    • Organolithium: Selectivity for Synthesis
    • Clayden J. Organolithium: Selectivity for Synthesis. Tetrahedron Organic Series. 23:2002;241-271.
    • (2002) Tetrahedron Organic Series , vol.23 , pp. 241-271
    • Clayden, J.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.