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Volumn 47, Issue 9, 2008, Pages 1726-1728

Palladium-catalyzed three-component approach to promazine with formation of one carbon-sulfur and two carbon-nitrogen bonds

Author keywords

Aryl amination; Homogeneous catalysis; Multicomponent reactions; Palladium; Sulfur heterocycles

Indexed keywords

AMINATION; IRON COMPOUNDS; ORGANIC COMPOUNDS; PALLADIUM; SULFUR;

EID: 41049099165     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200705209     Document Type: Article
Times cited : (114)

References (33)
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    • This reaction was first reported in a catalytic version in 1986: N. V. Kondratenko, A. Kolomeitsev, V. O. Mogilevskaya, N. M. Varlamova, L. M. Yagupol'skii, Zh. Org. Khim. 1986, 8, 1721-1729
    • This reaction was first reported in a catalytic version in 1986: N. V. Kondratenko, A. Kolomeitsev, V. O. Mogilevskaya, N. M. Varlamova, L. M. Yagupol'skii, Zh. Org. Khim. 1986, 8, 1721-1729
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    • translation
    • (English translation: J. Org. Chem. USSR 1986, 22, 1547-1554).
    • (1986) J. Org. Chem. USSR , vol.22 , pp. 1547-1554
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    • For a general discussion, see:, 3rd ed, Eds, P. Krogsgaard-Larsen, T. Liljefors, U. Madsen, Taylor and Francis, London, UK, chap. 11
    • For a general discussion, see: K. P. Bøgesø, B. Bang-Andersen in Textbook of Drug Design and Discovery, 3rd ed. (Eds.: P. Krogsgaard-Larsen, T. Liljefors, U. Madsen), Taylor and Francis, London, UK, 2002, chap. 11.
    • (2002) Textbook of Drug Design and Discovery
    • Bøgesø, K.P.1    Bang-Andersen in, B.2
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    • 53549087481 scopus 로고    scopus 로고
    • Abbreviations: bmim, n-butylmethyl imidazolium; binap, 2,2′-bis(diphenylphosphanyl)-1,1′-binaphthyl; davephos, 2-dicyclohexylphosphanyl-2′-(N,N-dimethylamino)biphenyl; dba, dibenzylidine acetone; dpephos, bis(2-diphenylphosphanyl)-ether; dppf, 1,1′-bis(diphenylphosphanyl)ferrocene; xantphos, 4,5- bis(diphenylphosphanyl)-9,9-dimethylxanthene; x-phos, 2-dicyclohexylphosphanyl- 2′,4′-6′-triisopropyl-1,1′-biphenyl
    • Abbreviations: bmim = (n-butyl)methyl imidazolium; binap = 2,2′-bis(diphenylphosphanyl)-1,1′-binaphthyl; davephos = 2-dicyclohexylphosphanyl-2′-(N,N-dimethylamino)biphenyl; dba = dibenzylidine acetone; dpephos = bis(2-diphenylphosphanyl)-ether; dppf = 1,1′-bis(diphenylphosphanyl)ferrocene; xantphos = 4,5- bis(diphenylphosphanyl)-9,9-dimethylxanthene; x-phos = 2-dicyclohexylphosphanyl- 2′,4′-6′-triisopropyl-1,1′-biphenyl.
  • 20
    • 53549134205 scopus 로고    scopus 로고
    • The reagents had to be mixed immediately before starting the reactions to avoid catalyst deactivation. Therefore, the classic oil bath conditions were more practical for ligand screening experiments see the Supporting Information for details, All chemicals were weighed out in air without precautions to exclude air from the reaction mixture
    • The reagents had to be mixed immediately before starting the reactions to avoid catalyst deactivation. Therefore, the classic oil bath conditions were more practical for ligand screening experiments (see the Supporting Information for details). All chemicals were weighed out in air without precautions to exclude air from the reaction mixture.
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    • 2].
    • 2].
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    • 5% of 3-methylindole is formed under these reaction conditions. We have optimized this serendipitous finding to a one-flask approach to 3-substituted indoles. T. Jensen, H. Pedersen, B. Bang-Andersen, R. Madsen, M. Jørgensen, Angew. Chem. 2008, 120, 902-904;
    • 5% of 3-methylindole is formed under these reaction conditions. We have optimized this serendipitous finding to a one-flask approach to 3-substituted indoles. T. Jensen, H. Pedersen, B. Bang-Andersen, R. Madsen, M. Jørgensen, Angew. Chem. 2008, 120, 902-904;
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    • Angew. Chem. Int. Ed. 2008, 47, 880-890..
    • (2008) Angew. Chem. Int. Ed , vol.47 , pp. 880-890
  • 33
    • 53549092468 scopus 로고    scopus 로고
    • No amination products formed with 4-(trifluoromethyl)aniline, 4-amino-benzoic acid ethyl ester, or 4-(dimethylamino)aniline
    • No amination products formed with 4-(trifluoromethyl)aniline, 4-amino-benzoic acid ethyl ester, or 4-(dimethylamino)aniline.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.