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Volumn 14, Issue 16, 2008, Pages 4961-4973

Selective formation of 2-imidazolines and 2-substituted oxazoles by using a three-component reaction

Author keywords

Heterocycles; Imidazolines; Multicomponent reactions; Oxazoles; Selectivity

Indexed keywords

ACIDS; ALDEHYDES; AMIDES; AMINES; ESTERS; KETONES; SILVER;

EID: 53849096036     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200800271     Document Type: Article
Times cited : (92)

References (64)
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    • 1 increases the a acidity and terminal C electrophilicity of the isocyanide (also see ref. [6b]).
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    • For a recent overview of the synthesis and reactions of oxazoles as well as oxazole-containing natural products, see: a) D. C. Palmer, Oxazoles: Synthesis, Reactions, and Spectroscopy, part A, Wiley, New Jersey (USA), 2003;
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    • I makes the (free) electron pair less reactive towards reaction with the imine (Scheme 2, path III).
    • I makes the (free) electron pair less reactive towards reaction with the imine (Scheme 2, path III).
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    • 3N) for the synthesis of 4n and 5n (Table 6, entry 5).
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    • Although no direct evidence for the formation of isocyanobenzyl-amide is observed and direct transamidation is usually only very limited (M. A. Kraus, Synthesis 1973, 361-362)
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    • fusion of ammonium salts with amides has been reported before (A. Galat, G. Elion, J. Am. Chem. Soc. 1943, 65, 1566-1567).
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    • I, see: C. Gonzalez-Arellano, A. Corma, M. Iglesias, F. Sánchez, Chem. Commun. 2005, 3451-3453;
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    • I catalysis, see: D. Benito-Garagorri, V. Bocokić, K. Kirchner, Tetrahedron Lett. 2006, 47, 8641-8644.
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    • Previously, ketones were found to yield the corresponding 2-(hydroxyalkyl)oxazoles, see ref, 9k
    • Previously, ketones were found to yield the corresponding 2-(hydroxyalkyl)oxazoles, see ref. [9k].
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    • I catalysis, most likely because of the intrinsically lower nucleophilicity of the ester carbonyl oxygen in 1 d-j compared with the amide carbonyl oxygen in 1c.
    • I catalysis, most likely because of the intrinsically lower nucleophilicity of the ester carbonyl oxygen in 1 d-j compared with the amide carbonyl oxygen in 1c.
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    • Synthesized according to the method reported: F. P. Doyle, G. R. Fosker, J. H. C. Nayler, H. Smith, J. Chem. Soc. 1962, 1440-1444.
    • Synthesized according to the method reported: F. P. Doyle, G. R. Fosker, J. H. C. Nayler, H. Smith, J. Chem. Soc. 1962, 1440-1444.
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    • 13C NMR spectrum for these type of compounds, also see ref. [6a].
    • 13C NMR spectrum for these type of compounds, also see ref. [6a].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.