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Volumn 345, Issue 4, 2003, Pages 483-487

Novel Reductive Amination of Nitriles: An Efficient Route to 5-Hydroxypiperidone-Derived N,N-Acetals

Author keywords

(S) HbHNL; Cyanohydrin; Hydroxylactam; N,N acetals; Nitrile hydrogenation

Indexed keywords

5 HYDROXYPIPERIDIN 2 ONE; ACETAL DERIVATIVE; CYANOHYDRIN; PIPERIDONE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0242522450     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200390054     Document Type: Article
Times cited : (28)

References (23)
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    • For recent syntheses of pseudoconhydrine, see: a) S. J. Hedley, W. J. Moran, A. H. G. P. Prenzel, D. A. Price, J. P. A. Harrity, Synlett 2001, 1596-1598; b) J. Löfstedt, H. Pettersson-Fasth, J.-E. Bäckvall, Tetrahedron 2000, 56, 2225-2230; c) G. Agami, F. Couty, H. Lam, H. Mathieu, Tetrahedron 1998, 54, 8783-8796; d) C. Herdeis, W. A. Held, A. Kirfel, F. Schwabenländer, Liebigs Ann 1995, 1293-1301.
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    • 0242634593 scopus 로고
    • For recent syntheses of pseudoconhydrine, see: a) S. J. Hedley, W. J. Moran, A. H. G. P. Prenzel, D. A. Price, J. P. A. Harrity, Synlett 2001, 1596-1598; b) J. Löfstedt, H. Pettersson-Fasth, J.-E. Bäckvall, Tetrahedron 2000, 56, 2225-2230; c) G. Agami, F. Couty, H. Lam, H. Mathieu, Tetrahedron 1998, 54, 8783-8796; d) C. Herdeis, W. A. Held, A. Kirfel, F. Schwabenländer, Liebigs Ann 1995, 1293-1301.
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    • Aldehyde 3 was prepared via ozonolysis of cycloocta-1,5-diene; for a similar procedure, see: M. A. Ciufolini, S. Zhu, J. Org. Chem. 1998, 63, 1668-1675.
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    • PhD Thesis, Technical University of Graz
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    • note
    • All new compounds were obtained as analytically pure compounds and have been adequately characterized using NMR, IR, and MS techniques.
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    • For a related example of N-methylation of a α-substituted nitrile, see: a) F. B. Cooling, S. K. Fager, R. D. Fallon, P. W. Folsom, F. G. Gallagher, J. E. Gavagan, F. E. Herkes, E. C. Hann, R. L. Phillips, A. Sigmund, L. W. Wagner, W. Wu, R. DiCosimo, J. Mol. Cat. B 2001, 11, 295-306; b) J. E. Gavagan, S. K. Fager, R. D. Fallon, P. W. Folsom, F. E. Herkes, A. Eisenberg, E. C. Hann, R. DiCosimo, J. Org. Chem. 1998, 63, 4792-4801.
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    • Gavagan, J.E.1    Fager, S.K.2    Fallon, R.D.3    Folsom, P.W.4    Herkes, F.E.5    Eisenberg, A.6    Hann, E.C.7    DiCosimo, R.8
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    • note
    • Crystallographic data (excluding structure factors) have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication CCDC 197096.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.