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Volumn 44, Issue 45, 2003, Pages 8221-8225

Pd/C mediated synthesis of 2-substituted benzo[b]furans/nitrobenzo[b] furans in water

Author keywords

Benzo b furans; Palladium catalyst; Sonogashira coupling 5 endo dig cyclization; Water

Indexed keywords

ALKYNE DERIVATIVE; BENZOFURAN DERIVATIVE; CARBON; COPPER DERIVATIVE; FUNCTIONAL GROUP; LIGAND; PALLADIUM; PHENOL DERIVATIVE; PHOSPHORUS DERIVATIVE; SOLVENT; WATER;

EID: 0141888366     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.09.080     Document Type: Article
Times cited : (106)

References (68)
  • 36
    • 0037226411 scopus 로고    scopus 로고
    • (r) For use of an aqueous alkyne-based palladium catalyzed reaction to produce benzofurans, see: Uozumi, Y.; Kobayashi, Y. Heterocycles 2003, 59, 71-74.
    • (2003) Heterocycles , vol.59 , pp. 71-74
    • Uozumi, Y.1    Kobayashi, Y.2
  • 37
    • 0038362007 scopus 로고    scopus 로고
    • For Pd-free synthesis of 2-arylbenzo[b]furans via Cu-catalyzed reaction see: and references cited therein
    • For Pd-free synthesis of 2-arylbenzo[b]furans via Cu-catalyzed reaction see: Bates C.G., Saejueng P., Murphy J.M., Venkataraman D. Org. Lett. 4:2002;4727-4729. and references cited therein.
    • (2002) Org. Lett. , vol.4 , pp. 4727-4729
    • Bates, C.G.1    Saejueng, P.2    Murphy, J.M.3    Venkataraman, D.4
  • 41
    • 0002389108 scopus 로고
    • (d) For palladium mediated reaction of 4-iodo-2-nitroresorcinol with terminal alkynes leading to the formation of 1,3-diynes see; Kundu, N. G.; Pal, M.; Chowdhury, C. J. Chem. Res. (S) 1993, 432-433;
    • (1993) J. Chem. Res. (S) , pp. 432-433
    • Kundu, N.G.1    Pal, M.2    Chowdhury, C.3
  • 42
    • 0002475963 scopus 로고
    • (e) For Pd/Cu-catalyzed reaction of 2,4,6-triiodophenol with phenylethyne leading to the formation of uncyclized product see: Tao, W.; Nesbitt, S.; Heck, R. F. J. Org. Chem. 1990, 55, 63-69.
    • (1990) J. Org. Chem. , vol.55 , pp. 63-69
    • Tao, W.1    Nesbitt, S.2    Heck, R.F.3
  • 54
    • 0003144752 scopus 로고    scopus 로고
    • Pal M., Kundu N.G. J. Chem. Soc., Perkin Trans. 1. 1996;449-451 Pal, M.; Parasuraman, K.; Yeleswarapu, K. R. Presented at the ACS meeting, 2003, New Orleans, Paper no. ORGN 590 Pal, M.; Subramanian, V.; Parasuraman, K.; Yeleswarapu, K. R. submitted for publication.
    • (1996) J. Chem. Soc., Perkin Trans. 1 , pp. 449-451
    • Pal, M.1    Kundu, N.G.2
  • 55
    • 0039452499 scopus 로고    scopus 로고
    • The o-hydroxytolan IIIaa isolated was found to be a stable compound and no spontaneous cyclization was observed upon storage at room temperature as reported earlier in other cases. For example o-hydroxytolan used for the synthesis of XH-14, a benzofuran derivative isolated from the plant Salvia miltiorrhiza, showed a strong tendency to cyclize even upon storage at 4°C. See Lutjens, H.; Scammells, P. J. Synlett 1999, 1079-1081.
    • (1999) Synlett , pp. 1079-1081
    • Lutjens, H.1    Scammells, P.J.2
  • 56
    • 0025037667 scopus 로고
    • For alternative access to nitrobenzo[b]furans via intramolecular condensation of suitably substituted nitrobenzenes, including intramolecular Wittig olefinations, see
    • Synthesis via direct nitration of benzo[b]furans often gives a mixture of isomers. See, for example: (a) Graham, S. L.; Hoffman, J. M.; Gautheron, P.; Michelson, S. R.; Scholz, T. H.; Schwam, H.; Shepard, K. L.; Smith, A. M.; Smith, R. L.; Sondey, J. M.; Sugrue, M. F. J. Med. Chem. 1990, 33, 749-754. For alternative access to nitrobenzo[b]furans via intramolecular condensation of suitably substituted nitrobenzenes, including intramolecular Wittig olefinations, see: (b) Chilin, A.; Rodighiero, P.; Guitto, A. Synthesis 1998, 309-313; (c) Kaminsky, D.; Shavel, F.; Meitzer, I. Tetrahedron Lett. 1967, 859-861; (d) Mooradian, A. Tetrahedron Lett. 1967, 407-408. (e) Mooradian, A.; Dupont, P. E. J. Heterocycl. Chem. 1967, 4, 441-444.
    • (1990) J. Med. Chem. , vol.33 , pp. 749-754
    • Graham, S.L.1    Hoffman, J.M.2    Gautheron, P.3    Michelson, S.R.4    Scholz, T.H.5    Schwam, H.6    Shepard, K.L.7    Smith, A.M.8    Smith, R.L.9    Sondey, J.M.10    Sugrue, M.F.11
  • 57
    • 0031931067 scopus 로고    scopus 로고
    • Synthesis via direct nitration of benzo[b]furans often gives a mixture of isomers. See, for example: (a) Graham, S. L.; Hoffman, J. M.; Gautheron, P.; Michelson, S. R.; Scholz, T. H.; Schwam, H.; Shepard, K. L.; Smith, A. M.; Smith, R. L.; Sondey, J. M.; Sugrue, M. F. J. Med. Chem. 1990, 33, 749-754. For alternative access to nitrobenzo[b]furans via intramolecular condensation of suitably substituted nitrobenzenes, including intramolecular Wittig olefinations, see: (b) Chilin, A.; Rodighiero, P.; Guitto, A. Synthesis 1998, 309-313; (c) Kaminsky, D.; Shavel, F.; Meitzer, I. Tetrahedron Lett. 1967, 859-861; (d) Mooradian, A. Tetrahedron Lett. 1967, 407-408. (e) Mooradian, A.; Dupont, P. E. J. Heterocycl. Chem. 1967, 4, 441-444.
    • (1998) Synthesis , pp. 309-313
    • Chilin, A.1    Rodighiero, P.2    Guitto, A.3
  • 58
    • 0011414135 scopus 로고
    • Synthesis via direct nitration of benzo[b]furans often gives a mixture of isomers. See, for example: (a) Graham, S. L.; Hoffman, J. M.; Gautheron, P.; Michelson, S. R.; Scholz, T. H.; Schwam, H.; Shepard, K. L.; Smith, A. M.; Smith, R. L.; Sondey, J. M.; Sugrue, M. F. J. Med. Chem. 1990, 33, 749-754. For alternative access to nitrobenzo[b]furans via intramolecular condensation of suitably substituted nitrobenzenes, including intramolecular Wittig olefinations, see: (b) Chilin, A.; Rodighiero, P.; Guitto, A. Synthesis 1998, 309-313; (c) Kaminsky, D.; Shavel, F.; Meitzer, I. Tetrahedron Lett. 1967, 859-861; (d) Mooradian, A. Tetrahedron Lett. 1967, 407-408. (e) Mooradian, A.; Dupont, P. E. J. Heterocycl. Chem. 1967, 4, 441-444.
    • (1967) Tetrahedron Lett. , pp. 859-861
    • Kaminsky, D.1    Shavel, F.2    Meitzer, I.3
  • 59
    • 0002318130 scopus 로고
    • Synthesis via direct nitration of benzo[b]furans often gives a mixture of isomers. See, for example: (a) Graham, S. L.; Hoffman, J. M.; Gautheron, P.; Michelson, S. R.; Scholz, T. H.; Schwam, H.; Shepard, K. L.; Smith, A. M.; Smith, R. L.; Sondey, J. M.; Sugrue, M. F. J. Med. Chem. 1990, 33, 749-754. For alternative access to nitrobenzo[b]furans via intramolecular condensation of suitably substituted nitrobenzenes, including intramolecular Wittig olefinations, see: (b) Chilin, A.; Rodighiero, P.; Guitto, A. Synthesis 1998, 309-313; (c) Kaminsky, D.; Shavel, F.; Meitzer, I. Tetrahedron Lett. 1967, 859-861; (d) Mooradian, A. Tetrahedron Lett. 1967, 407-408. (e) Mooradian, A.; Dupont, P. E. J. Heterocycl. Chem. 1967, 4, 441-444.
    • (1967) Tetrahedron Lett. , pp. 407-408
    • Mooradian, A.1
  • 60
    • 84981855973 scopus 로고
    • Synthesis via direct nitration of benzo[b]furans often gives a mixture of isomers. See, for example: (a) Graham, S. L.; Hoffman, J. M.; Gautheron, P.; Michelson, S. R.; Scholz, T. H.; Schwam, H.; Shepard, K. L.; Smith, A. M.; Smith, R. L.; Sondey, J. M.; Sugrue, M. F. J. Med. Chem. 1990, 33, 749-754. For alternative access to nitrobenzo[b]furans via intramolecular condensation of suitably substituted nitrobenzenes, including intramolecular Wittig olefinations, see: (b) Chilin, A.; Rodighiero, P.; Guitto, A. Synthesis 1998, 309-313; (c) Kaminsky, D.; Shavel, F.; Meitzer, I. Tetrahedron Lett. 1967, 859-861; (d) Mooradian, A. Tetrahedron Lett. 1967, 407-408. (e) Mooradian, A.; Dupont, P. E. J. Heterocycl. Chem. 1967, 4, 441-444.
    • (1967) J. Heterocycl. Chem. , vol.4 , pp. 441-444
    • Mooradian, A.1    Dupont, P.E.2
  • 63
    • 0000906980 scopus 로고    scopus 로고
    • All the terminal alkynes used are commercially available
    • 5 requires C, 63.36; H, 5.65%.
  • 64
    • 0000906980 scopus 로고    scopus 로고
    • note
    • 5 requires C, 63.36; H, 5.65%.
  • 65
    • 84988204469 scopus 로고
    • Use of other amine bases e.g. DBU, DBACO, DBN etc. in Sonogashira-type reactions has been previously reported
    • (a) Carpita, A.; Lessi, A.; Rossi, R. Synthesis 1984, 571-572. Use of other amine bases e.g. DBU, DBACO, DBN etc. in Sonogashira-type reactions has been previously reported:
    • (1984) Synthesis , pp. 571-572
    • Carpita, A.1    Lessi, A.2    Rossi, R.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.