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Volumn 44, Issue 34, 2003, Pages 6509-6511

Regiocontrolled synthesis of highly-functionalized fused imidazoles: A novel synthesis of second generation LFA-1 inhibitors

Author keywords

Imidazoles; LFA 1 inhibitors; Vinyl iodides

Indexed keywords

1H IMIDAZO[1,2 ALPHA]IMIDAZOL 2 ONE; IMIDAZOLE DERIVATIVE; LYMPHOCYTE FUNCTION ASSOCIATED ANTIGEN 1; UNCLASSIFIED DRUG;

EID: 0043199396     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01535-1     Document Type: Article
Times cited : (19)

References (27)
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    • 3PO, and the mechanistic implications of this observation are currently under investigation.
    • 3PO, and the mechanistic implications of this observation are currently under investigation.
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    • 2 failed to give any vinyl bromide analogous to 3 .
    • 2 failed to give any vinyl bromide analogous to 3 .
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    • For representative examples see: (a) Powers, J. C. J. Org. Chem. 1966, 31, 2627; (b) Russell, K.; Van Nivelt, C. E. J. Heterocycl. Chem. 1995, 32, 299; (c) Langley, B. W. J. Am. Chem. Soc. 1956, 2136; (d) Brennan, M. R.; Erickson, K. L.; Szmalc, F. S.; Tansey, M. J.; Thornton, J. M. Heterocycles 1986, 24, 2879; (e) Bendall, J. G.; Payne, A. N.; Screen, T. E. O.; Holmes, A. B. Chem. Commun. 1996, 11, 1067.
    • (1966) J. Org. Chem. , vol.31 , pp. 2627
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    • For representative examples see: (a) Powers, J. C. J. Org. Chem. 1966, 31, 2627; (b) Russell, K.; Van Nivelt, C. E. J. Heterocycl. Chem. 1995, 32, 299; (c) Langley, B. W. J. Am. Chem. Soc. 1956, 2136; (d) Brennan, M. R.; Erickson, K. L.; Szmalc, F. S.; Tansey, M. J.; Thornton, J. M. Heterocycles 1986, 24, 2879; (e) Bendall, J. G.; Payne, A. N.; Screen, T. E. O.; Holmes, A. B. Chem. Commun. 1996, 11, 1067.
    • (1995) J. Heterocycl. Chem. , vol.32 , pp. 299
    • Russell, K.1    Van Nivelt, C.E.2
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    • For representative examples see: (a) Powers, J. C. J. Org. Chem. 1966, 31, 2627; (b) Russell, K.; Van Nivelt, C. E. J. Heterocycl. Chem. 1995, 32, 299; (c) Langley, B. W. J. Am. Chem. Soc. 1956, 2136; (d) Brennan, M. R.; Erickson, K. L.; Szmalc, F. S.; Tansey, M. J.; Thornton, J. M. Heterocycles 1986, 24, 2879; (e) Bendall, J. G.; Payne, A. N.; Screen, T. E. O.; Holmes, A. B. Chem. Commun. 1996, 11, 1067.
    • (1956) J. Am. Chem. Soc. , pp. 2136
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    • For representative examples see: (a) Powers, J. C. J. Org. Chem. 1966, 31, 2627; (b) Russell, K.; Van Nivelt, C. E. J. Heterocycl. Chem. 1995, 32, 299; (c) Langley, B. W. J. Am. Chem. Soc. 1956, 2136; (d) Brennan, M. R.; Erickson, K. L.; Szmalc, F. S.; Tansey, M. J.; Thornton, J. M. Heterocycles 1986, 24, 2879; (e) Bendall, J. G.; Payne, A. N.; Screen, T. E. O.; Holmes, A. B. Chem. Commun. 1996, 11, 1067.
    • (1986) Heterocycles , vol.24 , pp. 2879
    • Brennan, M.R.1    Erickson, K.L.2    Szmalc, F.S.3    Tansey, M.J.4    Thornton, J.M.5
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    • For representative examples see: (a) Powers, J. C. J. Org. Chem. 1966, 31, 2627; (b) Russell, K.; Van Nivelt, C. E. J. Heterocycl. Chem. 1995, 32, 299; (c) Langley, B. W. J. Am. Chem. Soc. 1956, 2136; (d) Brennan, M. R.; Erickson, K. L.; Szmalc, F. S.; Tansey, M. J.; Thornton, J. M. Heterocycles 1986, 24, 2879; (e) Bendall, J. G.; Payne, A. N.; Screen, T. E. O.; Holmes, A. B. Chem. Commun. 1996, 11, 1067.
    • (1996) Chem. Commun. , vol.11 , pp. 1067
    • Bendall, J.G.1    Payne, A.N.2    Screen, T.E.O.3    Holmes, A.B.4
  • 25
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    • The TMSCl/NaI/water system generates HI in situ under mild conditions, and has been used for the synthesis of vinyl iodides via hydroiodination of alkynes, see: and references cited therein for further details
    • The TMSCl/NaI/water system generates HI in situ under mild conditions, and has been used for the synthesis of vinyl iodides via hydroiodination of alkynes, see: Kamiya N., Chikami Y., Ishii Y. Synlett. 1990;675. and references cited therein for further details.
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    • Kamiya, N.1    Chikami, Y.2    Ishii, Y.3
  • 26
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    • 3 to the reaction conditions resulted in various amounts of protodeiodination product 4.
    • Immediate quench of the reaction after completion was required, otherwise continuous exposure of the product 3 to the reaction conditions resulted in various amounts of protodeiodination product 4 .


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.