메뉴 건너뛰기




Volumn 70, Issue 16, 2005, Pages 6389-6397

Facile deallylation protocols for the preparation of N-unsubstituted triazoles and tetrazoles

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; COMPLEXATION; DERIVATIVES; ISOMERIZATION; NICKEL; REACTION KINETICS; RUTHENIUM COMPOUNDS; STOICHIOMETRY; SUBSTITUTION REACTIONS;

EID: 23044445796     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050836q     Document Type: Article
Times cited : (34)

References (72)
  • 1
    • 0011984675 scopus 로고
    • Schumann, E., Ed.; Thieme: Stuttgart
    • For, reviews on 1,2,3-triazoles, see: (a) Dehne, H. In Methoden der Organischen Chemie (Houben-Weyl); Schumann, E., Ed.; Thieme: Stuttgart, 1994; Vol. E8d, pp 305-405.
    • (1994) Methoden der Organischen Chemie (Houben-Weyl) , vol.E8D , pp. 305-405
    • Dehne, H.1
  • 2
    • 84943402961 scopus 로고
    • Katritzky, A. R., Rees, C. W., Eds.; Pergamon: Oxford
    • (b) Wamhoff, H. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon: Oxford, 1984; Vol. 5, pp 669-732.
    • (1984) Comprehensive Heterocyclic Chemistry , vol.5 , pp. 669-732
    • Wamhoff, H.1
  • 5
  • 6
    • 84943405513 scopus 로고
    • Katritzky, A. R., Rees, C. W., Eds.; Pergamon: Oxford
    • (b) Butler, R. N. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon: Oxford, 1984; Vol. 5, pp 791-838.
    • (1984) Comprehensive Heterocyclic Chemistry , vol.5 , pp. 791-838
    • Butler, R.N.1
  • 14
    • 4644340517 scopus 로고    scopus 로고
    • Recently, we have succeeded in synthesizing N-substituted triazoles and monosubstituted tetrazoles; see: (a) Jin, T.; Kamijo, S.; Yamamoto, Y. Eur. J. Org. Chem. 2004, 3789-3791 (triazole).
    • (2004) Eur. J. Org. Chem. , pp. 3789-3791
    • Jin, T.1    Kamijo, S.2    Yamamoto, Y.3
  • 27
    • 33544468067 scopus 로고    scopus 로고
    • In ref 10a; Chapter 7, pp 503-653
    • (a) In ref 10a; Chapter 7, pp 503-653.
  • 28
    • 33544470901 scopus 로고    scopus 로고
    • In ref 10b; Chapter 6, pp 185-243
    • (b) In ref 10b; Chapter 6, pp 185-243.
  • 29
    • 33544464923 scopus 로고    scopus 로고
    • For preliminary results, see: (a) Reference 4 (2-allyltriazole)
    • For preliminary results, see: (a) Reference 4 (2-allyltriazole).
  • 30
    • 33544472129 scopus 로고    scopus 로고
    • Reference 7b (2-allyltetrazole)
    • (b) Reference 7b (2-allyltetrazole).
  • 31
    • 0032568384 scopus 로고    scopus 로고
    • For reviews on reactions involving π-allylpalladium complexes, see: (a) Guibé, F. Tetrahedron 1998, 54, 2967-3042.
    • (1998) Tetrahedron , vol.54 , pp. 2967-3042
    • Guibé, F.1
  • 45
    • 33544454691 scopus 로고    scopus 로고
    • note
    • Due to the symmetrical structure of 2g, the position of a proton attached to nitrogen atom was easily determined; see the Supporting Information for details.
  • 46
    • 33544457638 scopus 로고    scopus 로고
    • note
    • Related mechanisms for nickel-catalyzed deallylation reactions; see ref 16b,c.
  • 47
    • 4544291000 scopus 로고    scopus 로고
    • For recent applications of a hydridonickel species in a catalytic reaction generated from a nickel complex and a Grignard reagent, see: (a) Milburn, R. R.; Snieckus, V. Angew. Chem., Int. Ed. 2004, 43, 888-891.
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 888-891
    • Milburn, R.R.1    Snieckus, V.2
  • 50
    • 33544459276 scopus 로고    scopus 로고
    • note
    • Analogous palladium intermediates are proposed in refs 3-7.
  • 51
    • 33847087023 scopus 로고
    • For representative transition metals used for isomerization of allylamines and/or allylamides, see: (a) Stille, J. K.; Becker, Y. J. Org. Chem. 1980, 45, 2139-2145 (Ru, Fe).
    • (1980) J. Org. Chem. , vol.45 , pp. 2139-2145
    • Stille, J.K.1    Becker, Y.2
  • 53
  • 64
    • 33544459974 scopus 로고    scopus 로고
    • In ref 10a, pp 574-576 and references therein
    • In ref 10a, pp 574-576 and references therein.
  • 65
    • 0032542132 scopus 로고    scopus 로고
    • Protecting groups for nitrogen-containing heteroaromatics, see: (a) Theodoridis, G. Tetrahedron Lett. 1998, 39, 9365-6368 (triazolinone).
    • (1998) Tetrahedron Lett. , vol.39 , pp. 9365-16368
    • Theodoridis, G.1
  • 69
    • 33544463119 scopus 로고    scopus 로고
    • note
    • Due to the symmetrical structure of 2i, the position of a proton attached to nitrogen atom was easily determined; see the Supporting Information for details.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.