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Volumn 43, Issue 4, 2004, Pages 478-482

An Efficient Synthesis of Bicyclic Amidines by Intramolecular Cyclization

Author keywords

Azides; Chirality; Cyclization; Nitrogen heterocycles

Indexed keywords

SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

EID: 0842329033     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200352750     Document Type: Article
Times cited : (58)

References (47)
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    • and references therein
    • For recent selected examples of 1,3-dipolar cycloadditions of azides, see: a) F. Himo, Z. P. Demko, L. Noodleman, K. B. Sharpless, J. Am. Chem. Soc. 2002, 124, 12 210, and references therein;
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    • Himo, F.1    Demko, Z.P.2    Noodleman, L.3    Sharpless, K.B.4
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    • d) for a related reaction of azides bearing an electron-withdrawing functional group and a highly strained enamine to afford amidines, see: J. K. Crandall, L. C. Crawley, J. B. Komin, J. Org. Chem. 1975, 40, 2045.
    • (1975) J. Org. Chem. , vol.40 , pp. 2045
    • Crandall, J.K.1    Crawley, L.C.2    Komin, J.B.3
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    • For examples of aza-Wittig cyclizations at an amide carbonyl, usually suffering from low yields, see: a) Y. G. Gololobov, N. I. Gusar, M. P. Chaus, Tetrahedron, 1985, 41, 1823;
    • (1985) Tetrahedron , vol.41 , pp. 1823
    • Gololobov, Y.G.1    Gusar, N.I.2    Chaus, M.P.3
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    • note
    • Confirmed by TLC and LC-MS analysis.
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    • 0842342428 scopus 로고    scopus 로고
    • note
    • In the thiolactam method, as illustrated in Scheme 1, at least four steps are required including nonproductive protection-depro-tection reactions because of the high reactivity of the amino functionality (see refs. [3a], [3b], and [6c] for details).
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    • 0842342418 scopus 로고    scopus 로고
    • note
    • For the preparation of starting material, see the Supporting Information.
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    • 0842299386 scopus 로고    scopus 로고
    • note
    • 13C NMR spectroscopy. Therefore, the cyclization step would be faster when oxalyl bromide is used.
  • 39
    • 0842277629 scopus 로고    scopus 로고
    • note
    • Synthetic procedure reported by Kotsuki et al. (in ref. [3a]) was as follows; 1. hydrogenation of the azide, 2. Boc protection of the resulting amine, 3. thioamide formation with Lawesson's reagent, 4. activation of thioamide (MeI) followed by Boc deprotection and cyclization (trifluoroacetic acid).
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    • For reviews, see: a) G. Köbrich, Angew. Chem. 1973, 85, 494; Angew. Chem. Int. Ed. Engl. 1973, 12, 464;
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    • Köbrich, G.1
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    • For reviews, see: a) G. Köbrich, Angew. Chem. 1973, 85, 494; Angew. Chem. Int. Ed. Engl. 1973, 12, 464;
    • (1973) Angew. Chem. Int. Ed. Engl. , vol.12 , pp. 464
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    • note
    • In situ IR spectra were recorded on a ReactIR 4000 instrument from ASI Applied Systems.
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    • note
    • -1 as a characteristic absorption. See the Supporting Information.
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    • note
    • ++H]) derived from 2·HBr.
  • 47
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    • note
    • Oxalyl bromide alone did not brominate anisole.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.