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Volumn 74, Issue 9, 2009, Pages 3286-3292

Regioselective syntheses of 2- and 4-formylpyrido[2,1-b]benzoxazoles

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ANHYDRIDES; FORMYLATION; OXAZOLE RING; PYRIDONE; REFLUXING; REGIO-SELECTIVE; REGIOSELECTIVE SYNTHESIS; VILSMEIER REAGENT;

EID: 66449104404     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900267c     Document Type: Article
Times cited : (26)

References (93)
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    • The Vilsmeier Reaction of Fully Conjugated Carbocycles and Heterocycles
    • For reviews, see: a, Paquette, L. A, Eds, John Wiley: New York
    • For reviews, see: (a) Jones, G.; Stanforth, S. P. The Vilsmeier Reaction of Fully Conjugated Carbocycles and Heterocycles. In Organic Reactions; Paquette, L. A., Eds.; John Wiley: New York, 1997; Vol. 49, pp 1-330.
    • (1997) Organic Reactions , vol.49 , pp. 1-330
    • Jones, G.1    Stanforth, S.P.2
  • 9
    • 66449124386 scopus 로고    scopus 로고
    • Jutz, C. Iminium Salts in Organic Chemistry. In AdVances in Organic Chemistry; Taylor, E. C., Ed.; John Wiley & Sons: New York, 1976; 9, Part I, pp 225-342.
    • (d) Jutz, C. Iminium Salts in Organic Chemistry. In AdVances in Organic Chemistry; Taylor, E. C., Ed.; John Wiley & Sons: New York, 1976; Vol. 9, Part I, pp 225-342.
  • 10
    • 36849009676 scopus 로고    scopus 로고
    • For recent and selective reports, see: a
    • For recent and selective reports, see: (a) Pinkerton, D. M.; Banwell, M. G.; Willis, A. C. Org. Lett. 2007, 9, 5127-5130.
    • (2007) Org. Lett , vol.9 , pp. 5127-5130
    • Pinkerton, D.M.1    Banwell, M.G.2    Willis, A.C.3
  • 18
    • 0000362560 scopus 로고    scopus 로고
    • The Vilsmeier Reaction of Non-Aromatic Compounds
    • For reviews, see: a, Jones, G, Stanforth, S. P, Eds, John Wiley: New York
    • For reviews, see: (a) Jones, G.; Stanforth, S. P. The Vilsmeier Reaction of Non-Aromatic Compounds. In Organic Reactions; Jones, G.; Stanforth, S. P., Eds.; John Wiley: New York, 2000; Vol. 56, pp 355-659.
    • (2000) Organic Reactions , vol.56 , pp. 355-659
    • Jones, G.1    Stanforth, S.P.2
  • 21
    • 0037244852 scopus 로고    scopus 로고
    • (d) Tasneem, Synlett 2003, 138-139.
    • (2003) Synlett , pp. 138-139
    • Tasneem1
  • 22
    • 0029163413 scopus 로고
    • (e) Balbi, A. Farmaco 1995, 50, 439-448.
    • (1995) Farmaco , vol.50 , pp. 439-448
    • Balbi, A.1
  • 73
    • 0000525422 scopus 로고
    • For selective reports, see: b
    • For selective reports, see: (b) Meth-Cohn, O.; Narine, B. Tetrahedron Lett. 1978, 19, 2045-2048.
    • (1978) Tetrahedron Lett , vol.19 , pp. 2045-2048
    • Meth-Cohn, O.1    Narine, B.2
  • 77
    • 0035961055 scopus 로고    scopus 로고
    • For selective examples about the application of the Meth-Cohn quinoline synthesis, see: f
    • For selective examples about the application of the Meth-Cohn quinoline synthesis, see: (f) Comins, D. L.; Nolan, J. M. Org. Lett. 2001, 3, 4255-4257.
    • (2001) Org. Lett , vol.3 , pp. 4255-4257
    • Comins, D.L.1    Nolan, J.M.2
  • 88
    • 66449111223 scopus 로고    scopus 로고
    • Crystal data for 5a: C12H7NO3, M 213.19, monoclinic, space group P2(1)/c, a) 9.0473(15) Å, b) 7.9725(13) Å, c) 13.064(2) Å, R ) 90 , ) 96.046(3) , ) 90′, V) 937.0(3) Å3, T) 292(2) K, Z) 4, Dc ) 1.511 g cm-3, μ(Mo KR) ) 0.111 mm-1, 5368 reflections measured, 2050 unique which were used in all calculations. R1 (all data) ) 0.0688. R1 ) 0.0496. CCDC 689518.
    • Crystal data for 5a: C12H7NO3, M) 213.19, monoclinic, space group P2(1)/c, a) 9.0473(15) Å, b) 7.9725(13) Å, c) 13.064(2) Å, R ) 90 , ) 96.046(3) , ) 90′, V) 937.0(3) Å3, T) 292(2) K, Z) 4, Dc ) 1.511 g cm-3, μ(Mo KR) ) 0.111 mm-1, 5368 reflections measured, 2050 unique which were used in all calculations. R1 (all data) ) 0.0688. R1 ) 0.0496. CCDC 689518.
  • 89
    • 66449134102 scopus 로고    scopus 로고
    • Crystal data for 6a: C12H7NO3, M) 213.19, triclinic, space group P-1, a 7.9660(18) Å, b) 9.582(2) Å, c) 13.056(3) Å, R ) 72.118(4) ,) 85.884(4) , A) 75.818(4) , V) 919.4(4) Å3, T) 293(2) K, Z) 4, Dc ) 1.540 g cm-3, μ(Mo KR) ) 0.113 mm-1, 3539 reflections measured, 2790 unique which were used in all calculations. R1 (all data) ) 0.0591. R1 ) 0.0502. CCDC 689517.
    • Crystal data for 6a: C12H7NO3, M) 213.19, triclinic, space group P-1, a) 7.9660(18) Å, b) 9.582(2) Å, c) 13.056(3) Å, R ) 72.118(4) ,) 85.884(4) , A) 75.818(4) , V) 919.4(4) Å3, T) 293(2) K, Z) 4, Dc ) 1.540 g cm-3, μ(Mo KR) ) 0.113 mm-1, 3539 reflections measured, 2790 unique which were used in all calculations. R1 (all data) ) 0.0591. R1 ) 0.0502. CCDC 689517.


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