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Volumn 43, Issue 32, 2004, Pages 4231-4233

Zirconium triflate catalyzed direct coupling reaction of lactams with heterocyclic arenes under atmospheric oxygen

Author keywords

C C coupling; Heteroarenes; Lactams; Lewis acids; Zirconium

Indexed keywords

CATALYSIS; CATALYSTS; DEHYDROGENATION; NITROGEN; OXYGEN; REACTION KINETICS;

EID: 4544376553     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200460429     Document Type: Article
Times cited : (50)

References (28)
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    • c) M. Bandini, A. Melloni, A. Umani-Ronchi, Angew. Chem. 2004, 116, 560-566; Angew. Chem. Int. Ed. 2004, 43, 550-556.
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    • note
    • 13C NMR spectroscopy and HRMS. For details, see supporting information.
  • 17
    • 4544355966 scopus 로고    scopus 로고
    • note
    • By-products based on 1a were detected by GC-MS analysis as 1-methylisatin (1-methylindole-2,3-dione), a dimer of la, and a trimer of 1a that bears a carbonyl function.
  • 18
    • 0001426611 scopus 로고    scopus 로고
    • (Eds.: A. R. Katritzky, C. W. Rees, E. F. V. Scriven, C. W. Bird), Pergamon, Oxford, chap. 2.03
    • a) R. J. Sundberg in Comprehensive Heterocyclic Chemistry II, Vol. 2 (Eds.: A. R. Katritzky, C. W. Rees, E. F. V. Scriven, C. W. Bird), Pergamon, Oxford, 1996, chap. 2.03, pp. 119-206;
    • (1996) Comprehensive Heterocyclic Chemistry II, Vol. 2 , vol.2 , pp. 119-206
    • Sundberg, R.J.1
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    • 0001275286 scopus 로고    scopus 로고
    • (Eds.: A. R. Katritzky, C. W. Rees, E. F. V. Scriven, C. W. Bird), Pergamon, Oxford, chap. 2.04
    • b) G. W. Gribble in Comprehensive Heterocyclic Chemistry II, Vol. 2 (Eds.: A. R. Katritzky, C. W. Rees, E. F. V. Scriven, C. W. Bird), Pergamon, Oxford, 1996, chap. 2.04, pp. 207-258.
    • (1996) Comprehensive Heterocyclic Chemistry II, Vol. 2 , pp. 207-258
    • Gribble, G.W.1
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    • 0032886581 scopus 로고    scopus 로고
    • TEMPO has been reportedly used as a radical scavenger; for example, see: a) I. Pallagi, A. Toró, G. Horváth, J. Org. Chem. 1999, 64, 6530-6540;
    • (1999) J. Org. Chem. , vol.64 , pp. 6530-6540
    • Pallagi, I.1    Toró, A.2    Horváth, G.3
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    • (Eds.: B. M. Trost, I. Fleming, C. H. Heathcock), Pergamon Press, Oxford, chap 45
    • It is well known that treatment of α-methoxyamides with Lewis acids generates cations stabilized by the lone pair of the nitrogen atom, N-acyliminium cations, to react with various nucleophiles: H. Hiemstra, W. N. Speckamp in Comprehensive Organic Synthesis, Vol. 2 (Eds.: B. M. Trost, I. Fleming, C. H. Heathcock), Pergamon Press, Oxford, 1991, chap. 4.5, pp. 1047-1082.
    • (1991) Comprehensive Organic Synthesis, Vol. 2 , vol.2 , pp. 1047-1082
    • Hiemstra, H.1    Speckamp, W.N.2
  • 28
    • 4544256655 scopus 로고    scopus 로고
    • Blackwell Science, Oxford
    • Electrophilic substitution of indoles is well known to take place at C3: J. A. Joule, K. Mills in Heterocyclic Chemistry, Blackwell Science, Oxford, 2000, pp. 324-379.
    • (2000) Mills in Heterocyclic Chemistry , pp. 324-379
    • Joule, J.A.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.