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Volumn 72, Issue 21, 2007, Pages 8087-8090

Copper(I)-catalyzed highly efficient synthesis of benzoselenazoles and benzotellurazoles

Author keywords

[No Author keywords available]

Indexed keywords

HETEROATOM SUBSTITUENT; ISOCYANIDES;

EID: 35348854372     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo7013164     Document Type: Article
Times cited : (85)

References (60)
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    • Reviews for pharmacological activities of selenium-containing heterocycles: a
    • Reviews for pharmacological activities of selenium-containing heterocycles: (a) Nogueira, C. W.; Zeni, G.; Rocha, J. B. T. Chem. Rev. 2004, 104, 6255-6286.
    • (2004) Chem. Rev , vol.104 , pp. 6255-6286
    • Nogueira, C.W.1    Zeni, G.2    Rocha, J.B.T.3
  • 43
    • 0009302853 scopus 로고    scopus 로고
    • Isocyanides are known to react with selenium and secondary amines in the presence of a base to give selenoureas: (a) Bulka, E, Ahlers, K. D, Tucek, E. Chem. Ber. 1967, 100, 1367-1372
    • Isocyanides are known to react with selenium and secondary amines in the presence of a base to give selenoureas: (a) Bulka, E.; Ahlers, K. D.; Tucek, E. Chem. Ber. 1967, 100, 1367-1372.
  • 46
    • 35348894074 scopus 로고    scopus 로고
    • The radical cyclization mechanism may be ruled out since when we performed the reaction in the presence of TEMPO, radical scavenger, no radical species were trapped with TEMPO and 3a was formed quantitatively
    • The radical cyclization mechanism may be ruled out since when we performed the reaction in the presence of TEMPO, radical scavenger, no radical species were trapped with TEMPO and 3a was formed quantitatively.
  • 47
    • 35348893475 scopus 로고    scopus 로고
    • The oxidative addition mechanism was proposed in 2-aminothiazole synthesis by copper- and palladium-catalyzed intramolecular coupling reaction of o-haloarylthioureas, see ref 5e
    • The oxidative addition mechanism was proposed in 2-aminothiazole synthesis by copper- and palladium-catalyzed intramolecular coupling reaction of o-haloarylthioureas, see ref 5e.
  • 48
    • 49249152306 scopus 로고    scopus 로고
    • For earlier work on nickel-catalyzed coupling of vinyl sulfides with Grignard reagents: Okamura, H.; Miura, M.; Takei, H. Tetrahedron Lett. 1979, 43-46.
    • For earlier work on nickel-catalyzed coupling of vinyl sulfides with Grignard reagents: Okamura, H.; Miura, M.; Takei, H. Tetrahedron Lett. 1979, 43-46.
  • 49
    • 33750025618 scopus 로고    scopus 로고
    • For the synthesis of the related 2-aryl-1,3-benzothiazoles: a
    • For the synthesis of the related 2-aryl-1,3-benzothiazoles: (a) Bose, D. S.; Idrees, M. J. Org. Chem. 2006, 71, 8261-8263.
    • (2006) J. Org. Chem , vol.71 , pp. 8261-8263
    • Bose, D.S.1    Idrees, M.2
  • 54
    • 35348830654 scopus 로고    scopus 로고
    • Chem. Abstr. 1987, 109, 29967.
    • Chem. Abstr. 1987, 109, 29967.
  • 57
    • 35348841790 scopus 로고    scopus 로고
    • The present transformation is not affected by the amounts of CuI and additive very much. When the reactions were carried out by using 3 mol % of CuI or without HMPA, 12a was obtained in 69% and 70% NMR yields, respectively.
    • The present transformation is not affected by the amounts of CuI and additive very much. When the reactions were carried out by using 3 mol % of CuI or without HMPA, 12a was obtained in 69% and 70% NMR yields, respectively.
  • 58
    • 0038248549 scopus 로고    scopus 로고
    • For 2-amino-1,3-benzoselenazoles, see: a
    • For 2-amino-1,3-benzoselenazoles, see: (a) Lok, R.; Leone, R. E.; Williams, A. J. J. Org. Chem. 1996, 61, 3289-3297.
    • (1996) J. Org. Chem , vol.61 , pp. 3289-3297
    • Lok, R.1    Leone, R.E.2    Williams, A.J.3
  • 60
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    • For 2-thio-1,3-benzoselenazoles: (c) Casar, Z, Leban, I, Maréchal, A. M.-L, Lorcy, D. J. Chem. Soc, Perkin Trans. 2002, 1, 1568-1573. 2-Amino-1,3-tellurazoles were prepared by the reaction of TeC14 with aromatic ureas, see ref 18
    • 4 with aromatic ureas, see ref 18.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.