메뉴 건너뛰기




Volumn 6, Issue 16, 2004, Pages 2741-2744

Synthesis of quinolines, 2-quinolones, phenanthridines, and 6(5H)-phenanthridinones via palladium[0]-mediated Ullmann cross-coupling of 1-bromo-2-nitroarenes with β-halo-enals, -enones, or -esters

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC NITRO COMPOUND; CARBON; ESTER DERIVATIVE; PALLADIUM; PHENANTHRIDINE DERIVATIVE; QUINOLINE DERIVATIVE; QUINOLONE DERIVATIVE; TITANIUM TETRACHLORIDE;

EID: 4344622281     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0490375     Document Type: Article
Times cited : (137)

References (47)
  • 1
    • 84944031181 scopus 로고    scopus 로고
    • Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, Chapter 5.06
    • (a) Balasubramanian, M.; Keay, J. G. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1996; Vol. 5, Chapter 5.06, p 245.
    • (1996) Comprehensive Heterocyclic Chemistry II , vol.5 , pp. 245
    • Balasubramanian, M.1    Keay, J.G.2
  • 4
    • 84944067367 scopus 로고
    • Katritzky, A. R., Ress, C. W., Eds.; Pergamon Press: New York
    • (a) Jones, J. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Ress, C. W., Eds.; Pergamon Press: New York, 1984; Vol. 2, pp 395-510.
    • (1984) Comprehensive Heterocyclic Chemistry , vol.2 , pp. 395-510
    • Jones, J.1
  • 5
    • 0037123427 scopus 로고    scopus 로고
    • For examples of recently developed methods (other than the Friedländer approach) for the synthesis of quinolines, see: (b) Pouységu, L.; Avellan, A.-V.; Quideau, S. J. Org. Chem. 2002, 67, 3425. (c) Ichikawa, J.; Wada, Y.; Miyazaki, H.; Mori, T.; Kuroki, H. Org. Lett. 2003, 5, 1455. (d) Mehta, B. K.; Yanagisawa, K.; Shiro, M.; Kotsuki, H. Org. Lett. 2003, 5, 1605. (e) Du, W.; Curran, D. P. Org. Lett. 2003, 5, 1765.
    • (2002) J. Org. Chem. , vol.67 , pp. 3425
    • Pouységu, L.1    Avellan, A.-V.2    Quideau, S.3
  • 6
    • 0042265625 scopus 로고    scopus 로고
    • For examples of recently developed methods (other than the Friedländer approach) for the synthesis of quinolines, see: (b) Pouységu, L.; Avellan, A.-V.; Quideau, S. J. Org. Chem. 2002, 67, 3425. (c) Ichikawa, J.; Wada, Y.; Miyazaki, H.; Mori, T.; Kuroki, H. Org. Lett. 2003, 5, 1455. (d) Mehta, B. K.; Yanagisawa, K.; Shiro, M.; Kotsuki, H. Org. Lett. 2003, 5, 1605. (e) Du, W.; Curran, D. P. Org. Lett. 2003, 5, 1765.
    • (2003) Org. Lett. , vol.5 , pp. 1455
    • Ichikawa, J.1    Wada, Y.2    Miyazaki, H.3    Mori, T.4    Kuroki, H.5
  • 7
    • 0141629392 scopus 로고    scopus 로고
    • For examples of recently developed methods (other than the Friedländer approach) for the synthesis of quinolines, see: (b) Pouységu, L.; Avellan, A.-V.; Quideau, S. J. Org. Chem. 2002, 67, 3425. (c) Ichikawa, J.; Wada, Y.; Miyazaki, H.; Mori, T.; Kuroki, H. Org. Lett. 2003, 5, 1455. (d) Mehta, B. K.; Yanagisawa, K.; Shiro, M.; Kotsuki, H. Org. Lett. 2003, 5, 1605. (e) Du, W.; Curran, D. P. Org. Lett. 2003, 5, 1765.
    • (2003) Org. Lett. , vol.5 , pp. 1605
    • Mehta, B.K.1    Yanagisawa, K.2    Shiro, M.3    Kotsuki, H.4
  • 8
    • 0042730088 scopus 로고    scopus 로고
    • For examples of recently developed methods (other than the Friedländer approach) for the synthesis of quinolines, see: (b) Pouységu, L.; Avellan, A.-V.; Quideau, S. J. Org. Chem. 2002, 67, 3425. (c) Ichikawa, J.; Wada, Y.; Miyazaki, H.; Mori, T.; Kuroki, H. Org. Lett. 2003, 5, 1455. (d) Mehta, B. K.; Yanagisawa, K.; Shiro, M.; Kotsuki, H. Org. Lett. 2003, 5, 1605. (e) Du, W.; Curran, D. P. Org. Lett. 2003, 5, 1765.
    • (2003) Org. Lett. , vol.5 , pp. 1765
    • Du, W.1    Curran, D.P.2
  • 10
    • 0035912306 scopus 로고    scopus 로고
    • For recent examples of the Friedländer-type approach to quinolines, see: (b) Hsiao, Y.; Rivera, N. R.; Yasuda, N.; Hughes, D. L.; Reider, P. J. Org. Lett. 2001, 3, 1101. (c) Cho, C. S.; Kim, B. T.; Kim, T.-J. Shim, S. C. Chem. Commun. 2001, 2576. (d) Arcadi, A.; Chiarini, M.; Di Giuseppe, S.; Marinelli, F. Synlett 2003, 203. (e) Palimkar, S. S.; Siddiqui, S. A.; Daniel, T.; Lahoti, R. J.; Srinivasan, K. V. J. Org. Chem. 2003, 68, 9371. (f) McNaughton, B. R.; Miller, B. L. Org. Lett. 2003, 5, 4257. (g) Dormer, P. G.; Eng, K. K.; Farr, R. N.; Humphrey, G. R.; McWilliams, J. C.; Reider, P. J.; Sager, J. W.; Volante, R. P. J. Org. Chem. 2003, 68, 467.
    • (2001) Org. Lett. , vol.3 , pp. 1101
    • Hsiao, Y.1    Rivera, N.R.2    Yasuda, N.3    Hughes, D.L.4    Reider, P.J.5
  • 11
    • 0002240888 scopus 로고    scopus 로고
    • For recent examples of the Friedländer-type approach to quinolines, see: (b) Hsiao, Y.; Rivera, N. R.; Yasuda, N.; Hughes, D. L.; Reider, P. J. Org. Lett. 2001, 3, 1101. (c) Cho, C. S.; Kim, B. T.; Kim, T.-J. Shim, S. C. Chem. Commun. 2001, 2576. (d) Arcadi, A.; Chiarini, M.; Di Giuseppe, S.; Marinelli, F. Synlett 2003, 203. (e) Palimkar, S. S.; Siddiqui, S. A.; Daniel, T.; Lahoti, R. J.; Srinivasan, K. V. J. Org. Chem. 2003, 68, 9371. (f) McNaughton, B. R.; Miller, B. L. Org. Lett. 2003, 5, 4257. (g) Dormer, P. G.; Eng, K. K.; Farr, R. N.; Humphrey, G. R.; McWilliams, J. C.; Reider, P. J.; Sager, J. W.; Volante, R. P. J. Org. Chem. 2003, 68, 467.
    • (2001) Chem. Commun. , pp. 2576
    • Cho, C.S.1    Kim, B.T.2    Kim, T.-J.3    Shim, S.C.4
  • 12
    • 0037287085 scopus 로고    scopus 로고
    • For recent examples of the Friedländer-type approach to quinolines, see: (b) Hsiao, Y.; Rivera, N. R.; Yasuda, N.; Hughes, D. L.; Reider, P. J. Org. Lett. 2001, 3, 1101. (c) Cho, C. S.; Kim, B. T.; Kim, T.-J. Shim, S. C. Chem. Commun. 2001, 2576. (d) Arcadi, A.; Chiarini, M.; Di Giuseppe, S.; Marinelli, F. Synlett 2003, 203. (e) Palimkar, S. S.; Siddiqui, S. A.; Daniel, T.; Lahoti, R. J.; Srinivasan, K. V. J. Org. Chem. 2003, 68, 9371. (f) McNaughton, B. R.; Miller, B. L. Org. Lett. 2003, 5, 4257. (g) Dormer, P. G.; Eng, K. K.; Farr, R. N.; Humphrey, G. R.; McWilliams, J. C.; Reider, P. J.; Sager, J. W.; Volante, R. P. J. Org. Chem. 2003, 68, 467.
    • (2003) Synlett , pp. 203
    • Arcadi, A.1    Chiarini, M.2    Di Giuseppe, S.3    Marinelli, F.4
  • 13
    • 0344391969 scopus 로고    scopus 로고
    • For recent examples of the Friedländer-type approach to quinolines, see: (b) Hsiao, Y.; Rivera, N. R.; Yasuda, N.; Hughes, D. L.; Reider, P. J. Org. Lett. 2001, 3, 1101. (c) Cho, C. S.; Kim, B. T.; Kim, T.-J. Shim, S. C. Chem. Commun. 2001, 2576. (d) Arcadi, A.; Chiarini, M.; Di Giuseppe, S.; Marinelli, F. Synlett 2003, 203. (e) Palimkar, S. S.; Siddiqui, S. A.; Daniel, T.; Lahoti, R. J.; Srinivasan, K. V. J. Org. Chem. 2003, 68, 9371. (f) McNaughton, B. R.; Miller, B. L. Org. Lett. 2003, 5, 4257. (g) Dormer, P. G.; Eng, K. K.; Farr, R. N.; Humphrey, G. R.; McWilliams, J. C.; Reider, P. J.; Sager, J. W.; Volante, R. P. J. Org. Chem. 2003, 68, 467.
    • (2003) J. Org. Chem. , vol.68 , pp. 9371
    • Palimkar, S.S.1    Siddiqui, S.A.2    Daniel, T.3    Lahoti, R.J.4    Srinivasan, K.V.5
  • 14
    • 0344927986 scopus 로고    scopus 로고
    • For recent examples of the Friedländer-type approach to quinolines, see: (b) Hsiao, Y.; Rivera, N. R.; Yasuda, N.; Hughes, D. L.; Reider, P. J. Org. Lett. 2001, 3, 1101. (c) Cho, C. S.; Kim, B. T.; Kim, T.-J. Shim, S. C. Chem. Commun. 2001, 2576. (d) Arcadi, A.; Chiarini, M.; Di Giuseppe, S.; Marinelli, F. Synlett 2003, 203. (e) Palimkar, S. S.; Siddiqui, S. A.; Daniel, T.; Lahoti, R. J.; Srinivasan, K. V. J. Org. Chem. 2003, 68, 9371. (f) McNaughton, B. R.; Miller, B. L. Org. Lett. 2003, 5, 4257. (g) Dormer, P. G.; Eng, K. K.; Farr, R. N.; Humphrey, G. R.; McWilliams, J. C.; Reider, P. J.; Sager, J. W.; Volante, R. P. J. Org. Chem. 2003, 68, 467.
    • (2003) Org. Lett. , vol.5 , pp. 4257
    • McNaughton, B.R.1    Miller, B.L.2
  • 15
    • 0037462413 scopus 로고    scopus 로고
    • For recent examples of the Friedländer-type approach to quinolines, see: (b) Hsiao, Y.; Rivera, N. R.; Yasuda, N.; Hughes, D. L.; Reider, P. J. Org. Lett. 2001, 3, 1101. (c) Cho, C. S.; Kim, B. T.; Kim, T.-J. Shim, S. C. Chem. Commun. 2001, 2576. (d) Arcadi, A.; Chiarini, M.; Di Giuseppe, S.; Marinelli, F. Synlett 2003, 203. (e) Palimkar, S. S.; Siddiqui, S. A.; Daniel, T.; Lahoti, R. J.; Srinivasan, K. V. J. Org. Chem. 2003, 68, 9371. (f) McNaughton, B. R.; Miller, B. L. Org. Lett. 2003, 5, 4257. (g) Dormer, P. G.; Eng, K. K.; Farr, R. N.; Humphrey, G. R.; McWilliams, J. C.; Reider, P. J.; Sager, J. W.; Volante, R. P. J. Org. Chem. 2003, 68, 467.
    • (2003) J. Org. Chem. , vol.68 , pp. 467
    • Dormer, P.G.1    Eng, K.K.2    Farr, R.N.3    Humphrey, G.R.4    McWilliams, J.C.5    Reider, P.J.6    Sager, J.W.7    Volante, R.P.8
  • 18
    • 0036589259 scopus 로고    scopus 로고
    • For useful recent reviews on the Ullmann reaction, see: (c) Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359. (d) Nelson, T. D.; Crouch, R. D. Org. React. 2004, 63, 265.
    • (2002) Chem. Rev. , vol.102 , pp. 1359
    • Hassan, J.1    Sevignon, M.2    Gozzi, C.3    Schulz, E.4    Lemaire, M.5
  • 19
    • 0036589259 scopus 로고    scopus 로고
    • For useful recent reviews on the Ullmann reaction, see: (c) Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359. (d) Nelson, T. D.; Crouch, R. D. Org. React. 2004, 63, 265.
    • (2004) Org. React. , vol.63 , pp. 265
    • Nelson, T.D.1    Crouch, R.D.2
  • 29
    • 0027405816 scopus 로고
    • These compounds were prepared using modifications of the methods reported in the following papers: (a) Bovonsombat, P.; McNelis, E. Tetrahedron 1993, 49, 1525. (b) Piers, E.; Grierson, J. R.; Lau, K. C.; Nagakura, I. Can. J. Chem. 1982, 60, 210. Full details of these preparations will be reported in due course.
    • (1993) Tetrahedron , vol.49 , pp. 1525
    • Bovonsombat, P.1    McNelis, E.2
  • 30
    • 0000507346 scopus 로고
    • Full details of these preparations will be reported in due course
    • These compounds were prepared using modifications of the methods reported in the following papers: (a) Bovonsombat, P.; McNelis, E. Tetrahedron 1993, 49, 1525. (b) Piers, E.; Grierson, J. R.; Lau, K. C.; Nagakura, I. Can. J. Chem. 1982, 60, 210. Full details of these preparations will be reported in due course.
    • (1982) Can. J. Chem. , vol.60 , pp. 210
    • Piers, E.1    Grierson, J.R.2    Lau, K.C.3    Nagakura, I.4
  • 40
    • 4344600635 scopus 로고
    • Clemo, G. R.; Felton, D. G. I. J. Chem. Soc. 1951, 671; Chem. Abstr. 1951, 45, 9060c.
    • (1951) Chem. Abstr. , vol.45
  • 45
    • 4344579399 scopus 로고
    • Migachev, G. I.; Grekhova, N. G.; Terent'ev, A. M. Khimiya Geterotsiklicheskikh Soedinenii 1981, 388; Chem. Abstr. 1981, 95, 42866d.
    • (1981) Chem. Abstr. , vol.95


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.