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Volumn 64, Issue 25, 1999, Pages 9194-9200

Palladium-catalyzed cyclocarbonylation of o-iodophenols and 2-hydroxy-3- iodopyridine with heterocumulenes: Regioselective synthesis of benzo[e]-1,3- oxazin-4-one and pyrido[3,2-e]-1,3-oxazin-4-one derivatives

Author keywords

[No Author keywords available]

Indexed keywords

BENZO[E][1,3]OXAZIN 4 ONE DERIVATIVE; HALIDE; PALLADIUM; PYRIDO[3,2 E][1,3]OXAZIN 4 ONE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0032784805     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991256u     Document Type: Article
Times cited : (41)

References (58)
  • 23
    • 0344124277 scopus 로고    scopus 로고
    • Reference 2f
    • (h) Reference 2f.
  • 45
    • 0000852033 scopus 로고
    • Dimerization and trimerization of isocyanates were observed in the presence of base for the reaction at elevated temperature. See: Hofmann, A. W. Ber. 1860, 3, 761. Snape, H. L. J. Chem. Soc. 1886, 49, 254. Hofmann, A. W. Ber. 1885, 18, 764.
    • (1860) Ber. , vol.3 , pp. 761
    • Hofmann, A.W.1
  • 46
    • 0342745244 scopus 로고
    • Dimerization and trimerization of isocyanates were observed in the presence of base for the reaction at elevated temperature. See: Hofmann, A. W. Ber. 1860, 3, 761. Snape, H. L. J. Chem. Soc. 1886, 49, 254. Hofmann, A. W. Ber. 1885, 18, 764.
    • (1886) J. Chem. Soc. , vol.49 , pp. 254
    • Snape, H.L.1
  • 47
    • 0012881339 scopus 로고
    • Dimerization and trimerization of isocyanates were observed in the presence of base for the reaction at elevated temperature. See: Hofmann, A. W. Ber. 1860, 3, 761. Snape, H. L. J. Chem. Soc. 1886, 49, 254. Hofmann, A. W. Ber. 1885, 18, 764.
    • (1885) Ber. , vol.18 , pp. 764
    • Hofmann, A.W.1
  • 48
    • 0344986786 scopus 로고    scopus 로고
    • note
    • 3-dppb catalyst system, 5h was obtained in a small amount with byproducts.
  • 49
    • 33847088632 scopus 로고
    • For the mechanism of oxidative addition of aryl halides to palladium complexes; see: Stille, J. K.; Lau, K.S. Y. Acc. Chem. Res. 1976, 10, 434.
    • (1976) Acc. Chem. Res. , vol.10 , pp. 434
    • Stille, J.K.1    Lau, K.S.Y.2
  • 50
    • 0001357020 scopus 로고    scopus 로고
    • Inter- and intramolecular coordination of amine to palladium aryl halide complexes was shown to enhance the acidity of the NH bond. See: (a) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 4708. (b) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 197, 88232. (c) Louie, J.; Paul, F.; Hartwig, J. F. Organometallics 1996, 15, 2794.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 4708
    • Driver, M.S.1    Hartwig, J.F.2
  • 51
    • 0001357020 scopus 로고    scopus 로고
    • Inter- and intramolecular coordination of amine to palladium aryl halide complexes was shown to enhance the acidity of the NH bond. See: (a) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 4708. (b) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 197, 88232. (c) Louie, J.; Paul, F.; Hartwig, J. F. Organometallics 1996, 15, 2794.
    • (1997) J. Am. Chem. Soc. , vol.197 , pp. 88232
    • Driver, M.S.1    Hartwig, J.F.2
  • 52
    • 5844307923 scopus 로고    scopus 로고
    • Inter- and intramolecular coordination of amine to palladium aryl halide complexes was shown to enhance the acidity of the NH bond. See: (a) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 4708. (b) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 197, 88232. (c) Louie, J.; Paul, F.; Hartwig, J. F. Organometallics 1996, 15, 2794.
    • (1996) Organometallics , vol.15 , pp. 2794
    • Louie, J.1    Paul, F.2    Hartwig, J.F.3
  • 53
    • 0344124257 scopus 로고    scopus 로고
    • note
    • 2 and 1 mol % dppb under 300 psi CO in benzene at 100°C for 12 h.
  • 54
    • 2742522974 scopus 로고
    • The dimerization of isocyanates catalyzed by pyridine and its derivatives was described by: Wiley, P. F. J. Am. Chem. Soc. 1949, 71, 3746.
    • (1949) J. Am. Chem. Soc. , vol.71 , pp. 3746
    • Wiley, P.F.1
  • 57
    • 0344555818 scopus 로고
    • Wiley: New York
    • Dains, F. B.; Eberly, F. Organic Syntheses; Wiley: New York, 1943; Collect. Vol. 2, p 355.
    • (1943) Organic Syntheses , vol.2 COLLECT. VOL. , pp. 355
    • Dains, F.B.1    Eberly, F.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.