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Volumn 53, Issue 5, 2012, Pages 497-501

Palladium-catalyzed synthesis of benzo[c]pyrimido[1,6-a]azepine scaffold from Morita-Baylis-Hillman adducts: Intramolecular 6-arylation of uracil nucleus

Author keywords

6 Arylation; Benzo c pyrimido 1,6 a azepine; Morita Baylis Hillman adducts; Palladium; Uracil

Indexed keywords

AZEPINE DERIVATIVE; BENZO[C]PYRIMIDO[1,6 A]AZEPINE; PALLADIUM; UNCLASSIFIED DRUG; URACIL;

EID: 84355161826     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.11.085     Document Type: Article
Times cited : (18)

References (39)
  • 1
    • 38949172780 scopus 로고    scopus 로고
    • For our recent synthesis of indole-containing polycyclic compounds from Morita-Baylis-Hillman adducts, see
    • For our recent synthesis of indole-containing polycyclic compounds from Morita-Baylis-Hillman adducts, see: H.S. Lee, S.H. Kim, T.H. Kim, and J.N. Kim Tetrahedron Lett. 49 2008 1773 1776
    • (2008) Tetrahedron Lett. , vol.49 , pp. 1773-1776
    • Lee, H.S.1    Kim, S.H.2    Kim, T.H.3    Kim, J.N.4
  • 11
    • 45449098271 scopus 로고    scopus 로고
    • Chem. Abstr. 2007, 147, 257667.
    • (2007) Chem. Abstr. , vol.147 , pp. 257667
  • 14
    • 63849130632 scopus 로고    scopus 로고
    • For the palladium-catalyzed synthesis of 5-aryluracil derivatives with arylboron reagents, see
    • For the palladium-catalyzed synthesis of 5-aryluracil derivatives with arylboron reagents, see: L. Kalachova, R. Pohl, and M. Hocek Synthesis 2009 105 112
    • (2009) Synthesis , pp. 105-112
    • Kalachova, L.1    Pohl, R.2    Hocek, M.3
  • 20
    • 79955666014 scopus 로고    scopus 로고
    • For recent 6-arylation of uracil derivatives, see
    • For recent 6-arylation of uracil derivatives, see: Y.-C. Shih, and T.-C. Chien Tetrahedron 67 2011 3915 3923
    • (2011) Tetrahedron , vol.67 , pp. 3915-3923
    • Shih, Y.-C.1    Chien, T.-C.2
  • 21
    • 0028124707 scopus 로고
    • For the palladium-catalyzed synthesis of 5-aryluracil derivatives with arylstannane reagents, see
    • For the palladium-catalyzed synthesis of 5-aryluracil derivatives with arylstannane reagents, see: A.J. Gutierrez, T.J. Terhorst, M.D. Matteucci, and B.C. Froehler J. Am. Chem. Soc. 116 1994 5540 5544
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 5540-5544
    • Gutierrez, A.J.1    Terhorst, T.J.2    Matteucci, M.D.3    Froehler, B.C.4
  • 25
    • 67650711475 scopus 로고    scopus 로고
    • For the palladium-catalyzed intermolecular arylation of uracil derivatives, see
    • For the palladium-catalyzed intermolecular arylation of uracil derivatives, see: M. Cernova, R. Pohl, and M. Hocek Eur. J. Org. Chem. 2009 3698 3701
    • (2009) Eur. J. Org. Chem. , pp. 3698-3701
    • Cernova, M.1    Pohl, R.2    Hocek, M.3
  • 27
    • 60949108278 scopus 로고    scopus 로고
    • For the palladium-catalyzed intramolecular arylation of uracil derivatives, see
    • For the palladium-catalyzed intramolecular arylation of uracil derivatives, see: K.C. Majumdar, B. Sinha, P.K. Maji, and S.K. Chattopadhyay Tetrahedron 65 2009 2751 2756
    • (2009) Tetrahedron , vol.65 , pp. 2751-2756
    • Majumdar, K.C.1    Sinha, B.2    Maji, P.K.3    Chattopadhyay, S.K.4
  • 29
    • 80054870897 scopus 로고    scopus 로고
    • further references cited therein
    • K.H. Kim, H.S. Lee, and J.N. Kim Tetrahedron Lett. 52 2011 6228 6233 and further references cited therein
    • (2011) Tetrahedron Lett. , vol.52 , pp. 6228-6233
    • Kim, K.H.1    Lee, H.S.2    Kim, J.N.3
  • 30
    • 33846979513 scopus 로고    scopus 로고
    • For the difficulty in the Pd-catalyzed C-arylation of free (N-H)-containing heterocycles including free (N-H)-indoles and pyrroles, see:, In addition, the failure of C-arylation of uracil derivatives was also noted in Ref. 6
    • For the difficulty in the Pd-catalyzed C-arylation of free (N-H)-containing heterocycles including free (N-H)-indoles and pyrroles, see: X. Wang, D.V. Gribkov, and D. Sames J. Org. Chem. 72 2007 1476 1479 In addition, the failure of C-arylation of uracil derivatives was also noted in Ref. 6
    • (2007) J. Org. Chem. , vol.72 , pp. 1476-1479
    • Wang, X.1    Gribkov, D.V.2    Sames, D.3
  • 31
    • 0033179825 scopus 로고    scopus 로고
    • For the formal anti β-H elimination, and further references cited therein. Most of the intramolecular Heck reactions involving a formal anti-elimination process could be understood actually by syn β-H elimination after the epimerization of a carbopalladation intermediate via a palladium enolate or the epimerization of β-H
    • For the formal anti β-H elimination M. Ikeda, S.A.A. El Bialy, and T. Yakura Heterocycles 51 1999 1957 1970 and further references cited therein. Most of the intramolecular Heck reactions involving a formal anti-elimination process could be understood actually by syn β-H elimination after the epimerization of a carbopalladation intermediate via a palladium enolate or the epimerization of β-H
    • (1999) Heterocycles , vol.51 , pp. 1957-1970
    • Ikeda, M.1    El Bialy, S.A.A.2    Yakura, T.3
  • 35
    • 84986477080 scopus 로고
    • For some examples of Fujiwara-Moritani oxidative Heck reaction, see
    • For some examples of Fujiwara-Moritani oxidative Heck reaction, see: K. Hirota, Y. Isobe, Y. Kitade, and Y. Maki Synthesis 1987 495 496
    • (1987) Synthesis , pp. 495-496
    • Hirota, K.1    Isobe, Y.2    Kitade, Y.3    Maki, Y.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.