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Volumn 71, Issue 1, 2006, Pages 260-264

Orthogonal and auto-tandem catalysis: Synthesis of dipyrido[1,2-a:2′, 3′-d]imidazole and its benzo and aza analogues via inter- and intramolecular C-N bond formation

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CHEMICAL BONDS; NITROGEN; POLYCYCLIC AROMATIC HYDROCARBONS; SYNTHESIS (CHEMICAL);

EID: 31144444013     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052091u     Document Type: Article
Times cited : (75)

References (45)
  • 5
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    • Pergamon: Amsterdam
    • For examples of the decoration and construction of nitrogen-containing heterocycles via palladium-catalyzed C-C and C-N bond-forming reactions, see: (a) Li, J. J.; Gribble, G. W. Palladium in Heterocyclic Chemistry; Pergamon: Amsterdam, 2000.
    • (2000) Palladium in Heterocyclic Chemistry
    • Li, J.J.1    Gribble, G.W.2
  • 7
    • 0034603363 scopus 로고    scopus 로고
    • For examples of the synthesis of nitrogen-containing heterocycles via the use of an intramolecular Pd-catalyzed amination, see the following references. (a) For indoles, see: Brown, J. A. Tetrahedron Lett. 2000, 41, 1623.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 1623
    • Brown, J.A.1
  • 8
    • 0029874188 scopus 로고    scopus 로고
    • (b) For indolines, 1,2,3,4-tetrahydroquinoline and 2,3,4,5-tetrahydro-1H- 1-benzazepine, see: Wolfe, J. P.; Rennels, R. A.; Buchwald, S. L. Tetrahedron 1996, 52, 7525.
    • (1996) Tetrahedron , vol.52 , pp. 7525
    • Wolfe, J.P.1    Rennels, R.A.2    Buchwald, S.L.3
  • 15
    • 0038034710 scopus 로고    scopus 로고
    • For examples of tandem-catalyzed reactions that involve palladium-catalyzed C-N and C-C bond formation, see: (a) Yamazaki, K.; Nakamura, Y.; Kondo, Y. J. Org. Chem. 2003, 68, 6011.
    • (2003) J. Org. Chem. , vol.68 , pp. 6011
    • Yamazaki, K.1    Nakamura, Y.2    Kondo, Y.3
  • 26
    • 31144444179 scopus 로고    scopus 로고
    • note
    • The C-2 chemoselective amination on 1 was confirmed via a C-Br hydrogenolysis reaction on the obtained N-(3-bromopyridin-2-yl) azaheteroarylamines.
  • 27
    • 31144444420 scopus 로고    scopus 로고
    • Table A
    • For details, see Supporting Information. (a) Table A.
  • 28
    • 31144452001 scopus 로고    scopus 로고
    • Table B
    • (b) Table B.
  • 29
    • 31144436720 scopus 로고    scopus 로고
    • note
    • (c) Temperature measured inside the vessel (fiber optic probe). Oil bath temperature = 160 °C.
  • 30
    • 31144436467 scopus 로고    scopus 로고
    • Table C
    • (d) For attempts to perform auto-tandem Cu-catalyzed double amination, see Table C.
  • 32
    • 0033549829 scopus 로고    scopus 로고
    • DTPB = 2-(di-tert-butylphosphanyl)biphenyl (JohnPhos), DCPB = 2-(dicyclohexylphosphanyl)biphenyl, DCPAB (DavePhos) = 2-dicyclohexylphosphanyl- 2′-(N,N-dimethylamino)biphenyl. Wolfe, J. P.; Buchwald, S. L. Angew. Chem., Int. Ed. 1999, 38, 2413.
    • (1999) Angew. Chem., Int. Ed. , vol.38 , pp. 2413
    • Wolfe, J.P.1    Buchwald, S.L.2
  • 40
    • 31144477680 scopus 로고    scopus 로고
    • note
    • The intermolecular Pd-catalyzed amination of 1 with 2a was finished after 7 h, as judged by TLC and MS analysis.
  • 45
    • 31144438811 scopus 로고    scopus 로고
    • note
    • Trace amounts (<5%) of dipyrido[1,2-a:3′,2′-d]imidazole and its benzo and aza analogues were also isolated. These regioisomers are presumably formed via tandem C-3 intermolecular and C-2 intramolecular metal-catalyzed amination.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.