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Volumn 60, Issue 10, 2004, Pages 2311-2326

Multicomponent Hantzsch cyclocondensation as a route to highly functionalized 2- and 4-dihydropyridylalanines, 2- and 4-pyridylalanines, and their N-oxides: Preparation via a polymer-assisted solution-phase approach

Author keywords

Hantzsch reaction; Heterocyclic amino acids; Multicomponent reaction; Pyridyl alanines; Unnatural amino acids

Indexed keywords

ACETOACETIC ACID DERIVATIVE; ALANINE DERIVATIVE; ALDEHYDE DERIVATIVE; AMINE; AMINO ACID DERIVATIVE; GLYCINE DERIVATIVE; PEPTIDE DERIVATIVE; PHENYLALANINE DERIVATIVE; POLYMER;

EID: 1242328670     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.01.011     Document Type: Article
Times cited : (169)

References (70)
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    • Isolation: Ref. 12a.
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    • For improved one-pot oxidative conditions (Jones reagent) that transform this heterocycle into N-Boc glycinate without epimerization, see: (a)
    • For improved one-pot oxidative conditions (Jones reagent) that transform this heterocycle into N-Boc glycinate without epimerization, see: (a) Dondoni A., Mariotti G., Marra A. J. Org. Chem. 67:2002;4475-4486.
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    • 2, 0 (C, 1 h). The high reactivity of tert-butyl ester groups at C3 and C5 may be attributed to the strong conjugation with the adjacent carbon-carbon double bond of the enaminic system. This speculation is supported by the unreactivity under the above acidic conditions of tert-butyl ester groups installed at C3 and C5 of pyridyl and 1-oxido-pyridyl rings. For a discussion about this issue, see: (a)
    • 2, 0 (C, 1 h). The high reactivity of tert-butyl ester groups at C3 and C5 may be attributed to the strong conjugation with the adjacent carbon-carbon double bond of the enaminic system. This speculation is supported by the unreactivity under the above acidic conditions of tert-butyl ester groups installed at C3 and C5 of pyridyl and 1-oxido-pyridyl rings. For a discussion about this issue, see: (a) Goerlitzer K., Baltrusch H. J. Pharmazie. 10:2000;747-750.
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    • note
    • Complete crystallographic data (excluding structural factors) for the structure of the (R)-Mosher's amide of (4R)-27a have been deposited with the Cambridge Crystallographic Data Centre as supplementary publications number CCDC 222942. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(0)-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk ].
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    • Trost, B.M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.