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Volumn 72, Issue 18, 2007, Pages 6873-6877

Novel and convenient synthesis of substituted quinolines by copper- or palladium-catalyzed cyclodehydration of 1-(2-aminoaryl)-2-yn-1-ols

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; COPPER; DEHYDRATION; PALLADIUM; REACTION KINETICS; SYNTHESIS (CHEMICAL);

EID: 34548770580     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo071094z     Document Type: Article
Times cited : (120)

References (97)
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    • See, for example: a
    • See, for example: (a) Heitsch, H. Curr. Med. Chem. 2002, 9, 913-928.
    • (2002) Curr. Med. Chem , vol.9 , pp. 913-928
    • Heitsch, H.1
  • 30
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    • Monga, V.; Nayyar, A.; Vaitilingam, B.; Palde, P. B.; Jhamb, S. S.; Kaur, S.; Singh, P. P.; Jain, R. Bioorg. Med. Chem. 2004, 12, 6465-6472 (correction: 2005, 13, 1879)
    • (c) Monga, V.; Nayyar, A.; Vaitilingam, B.; Palde, P. B.; Jhamb, S. S.; Kaur, S.; Singh, P. P.; Jain, R. Bioorg. Med. Chem. 2004, 12, 6465-6472 (correction: 2005, 13, 1879)
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    • Bénard, C.; Zouhiri, F.; Normand-Bayle, M.; Danet, M.; Desmaële, D.; Leh, H.; Mouscadet, J. F.; Mbemba, G.; Thomas, C. M.; Bonnenfant, S.; Le, Bret, M.; d'Angelo, J. Bioorg. Med. Chem. Lett. 2004, 14, 2473-2476.
    • (b) Bénard, C.; Zouhiri, F.; Normand-Bayle, M.; Danet, M.; Desmaële, D.; Leh, H.; Mouscadet, J. F.; Mbemba, G.; Thomas, C. M.; Bonnenfant, S.; Le, Bret, M.; d'Angelo, J. Bioorg. Med. Chem. Lett. 2004, 14, 2473-2476.
  • 55
    • 33744470613 scopus 로고    scopus 로고
    • For some very recent developments in the synthesis of quinolines, see: b
    • For some very recent developments in the synthesis of quinolines, see: (b) Ichikawa, J.; Sakoda, K.; Moriyama, H.; Wada, Y. Synthesis 2006, 1590-1598.
    • (2006) Synthesis , pp. 1590-1598
    • Ichikawa, J.1    Sakoda, K.2    Moriyama, H.3    Wada, Y.4
  • 72
    • 33746146972 scopus 로고    scopus 로고
    • For recent leading examples, see: a
    • For recent leading examples, see: (a) Jia, C. S.; Wang, G. W. Lett. Org. Chem. 2006, 3, 289-291.
    • (2006) Lett. Org. Chem , vol.3 , pp. 289-291
    • Jia, C.S.1    Wang, G.W.2
  • 84
    • 34548709770 scopus 로고    scopus 로고
    • The formation of 6-chloro-2-cyclopropyl-4-trifluoromethylquinolin-5-ol from 3-amino-6-chloro-2-(3-cyclopropyl-1-hydroxy-1-trifluoromethylprop-2-ynyl) phenol, obtained in situ by deprotection of the corresponding tert-butyldimethylsilyl ether with TBAF, has been briefly mentioned in the literature as an undesired reaction, but no further experimental details (including the product yield) have been given for this reaction: (a) Markwalder, J. A.; Mutlib, D. D. C. A.; Cordova, B. C., Klabe, R. M.; Seitz, S. P. Bioorg. Med. Chem. Lett. 2001, 11, 619-622.
    • The formation of 6-chloro-2-cyclopropyl-4-trifluoromethylquinolin-5-ol from 3-amino-6-chloro-2-(3-cyclopropyl-1-hydroxy-1-trifluoromethylprop-2-ynyl) phenol, obtained in situ by deprotection of the corresponding tert-butyldimethylsilyl ether with TBAF, has been briefly mentioned in the literature as an undesired reaction, but no further experimental details (including the product yield) have been given for this reaction: (a) Markwalder, J. A.; Mutlib, D. D. C. A.; Cordova, B. C., Klabe, R. M.; Seitz, S. P. Bioorg. Med. Chem. Lett. 2001, 11, 619-622.
  • 85
    • 0034770833 scopus 로고    scopus 로고
    • Formation of 6-chloro-2-cyclopropyl-4-trifluoromethylquinoline in 81% yield by refluxing a solution of 2-(2-amino-5-chlorophenyl)-4-cyclopropyl-1,1,1- trifluorobut-3-yn-2-ol in chlorobenzene for 6 h has also been reported: (b) Choudhury, A.; Pierce, M. E.; Confalone, P. N. Synth. Commun. 2001, 31, 3707-3714.
    • Formation of 6-chloro-2-cyclopropyl-4-trifluoromethylquinoline in 81% yield by refluxing a solution of 2-(2-amino-5-chlorophenyl)-4-cyclopropyl-1,1,1- trifluorobut-3-yn-2-ol in chlorobenzene for 6 h has also been reported: (b) Choudhury, A.; Pierce, M. E.; Confalone, P. N. Synth. Commun. 2001, 31, 3707-3714.
  • 86
    • 31544481845 scopus 로고    scopus 로고
    • The iodocyclization of 1-(2-dimethylaminophenyl)-2-yn-1-ols to give 4-hydroxy-3-iodo-1,1-dimethyl-1,4-dihydroquinolinium iodides, which, upon heating, underwent formal loss of MeOH to give 3-iodo-1-methylquinolinium iodides has been recently reported: Hessian, K. O.; Flynn, B. L. Org. Lett. 2006, 8, 243-246.
    • The iodocyclization of 1-(2-dimethylaminophenyl)-2-yn-1-ols to give 4-hydroxy-3-iodo-1,1-dimethyl-1,4-dihydroquinolinium iodides, which, upon heating, underwent formal loss of MeOH to give 3-iodo-1-methylquinolinium iodides has been recently reported: Hessian, K. O.; Flynn, B. L. Org. Lett. 2006, 8, 243-246.
  • 94
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    • Unidentified chromatographically immobile materials were formed as a result of decomposition
    • Unidentified chromatographically immobile materials were formed as a result of decomposition.
  • 95
    • 34548725110 scopus 로고    scopus 로고
    • 24 (see the Supporting Information for details). It is worth noting that in this latter case the authors have indicated the structure of the mononitrated product as 5-methoxy-2-nitroacetophenone rather than 3-methoxy-2-nitroacetophenone. The reduction of 3-methoxy-2-nitroacetophenone to give 2-amino-3-methoxyacetophenone was carried out as described in ref 24.
    • 24 (see the Supporting Information for details). It is worth noting that in this latter case the authors have indicated the structure of the mononitrated product as 5-methoxy-2-nitroacetophenone rather than 3-methoxy-2-nitroacetophenone. The reduction of 3-methoxy-2-nitroacetophenone to give 2-amino-3-methoxyacetophenone was carried out as described in ref 24.


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