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Volumn 72, Issue 11, 2007, Pages 4276-4279

A mild and efficient synthesis of 4-quinolones and quinolone heterocycles

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIZATION; REACTION KINETICS; SYNTHESIS (CHEMICAL);

EID: 34249826370     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070181o     Document Type: Article
Times cited : (126)

References (36)
  • 6
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    • Lucero, B. d'A.; Gomes, C. R. B.; Frugulhetti, I. C. de P. P.; Faro, L. V.; Alvarenga, L.; Souza, M. C. B. V.; de Souza, T. M. L. Ferreira, V. F. Bioorg. Med. Chem. Lett. 2006, 16, 1010-1013.
    • Lucero, B. d'A.; Gomes, C. R. B.; Frugulhetti, I. C. de P. P.; Faro, L. V.; Alvarenga, L.; Souza, M. C. B. V.; de Souza, T. M. L. Ferreira, V. F. Bioorg. Med. Chem. Lett. 2006, 16, 1010-1013.
  • 14
    • 33947087705 scopus 로고    scopus 로고
    • For reactions employing Eaton's reagent, refer to: (a) Eaton, P. E.; Carlson, G. R.; Lee, J. T. J. Org. Chem. 1973, 38, 4071-4073.
    • For reactions employing Eaton's reagent, refer to: (a) Eaton, P. E.; Carlson, G. R.; Lee, J. T. J. Org. Chem. 1973, 38, 4071-4073.
  • 17
    • 33745753488 scopus 로고    scopus 로고
    • During the preparation of this manuscript, a similar transformation of an o-iodoaniline intermediate at 90°C using Eaton's reagent was reported: Dorow, R. L.; Herrinton, P. M.; Hohler, R. A.; Maloney, M. T.; Mauragis, M. A.; McGhee, W. E.; Moeslein, J. A.; Strohbach, J. W.; Veley, M. F. Org. Process Res. Dev. 2006, 10, 493-499.
    • (d) During the preparation of this manuscript, a similar transformation of an o-iodoaniline intermediate at 90°C using Eaton's reagent was reported: Dorow, R. L.; Herrinton, P. M.; Hohler, R. A.; Maloney, M. T.; Mauragis, M. A.; McGhee, W. E.; Moeslein, J. A.; Strohbach, J. W.; Veley, M. F. Org. Process Res. Dev. 2006, 10, 493-499.
  • 18
    • 34249776535 scopus 로고    scopus 로고
    • 3H) was purchased from Sigma-Aldrich
    • 3H) was purchased from Sigma-Aldrich
  • 19
    • 46149138072 scopus 로고    scopus 로고
    • Gradient 1D NOESY using Gaussian excitation pulse and 500-600 ms mixing time: (a) Kessler, H.; Oschkinat, H.; Griesinger, C.; Bermel, W. J. J. Magn. Reson. 1986, 70, 106-133.
    • Gradient 1D NOESY using Gaussian excitation pulse and 500-600 ms mixing time: (a) Kessler, H.; Oschkinat, H.; Griesinger, C.; Bermel, W. J. J. Magn. Reson. 1986, 70, 106-133.
  • 23
    • 34249815675 scopus 로고    scopus 로고
    • Microwave-assisted synthesis of 1b was briefly explored and found to give product, albeit in poor yields.
    • (b) Microwave-assisted synthesis of 1b was briefly explored and found to give product, albeit in poor yields.
  • 24
    • 34249788591 scopus 로고    scopus 로고
    • 4, TFA, or HOAc at 50-100°C over prolonged period of time resulted in the recovery of substrate 1a along with significant amounts of hydrolysis product (aniline).
    • 4, TFA, or HOAc at 50-100°C over prolonged period of time resulted in the recovery of substrate 1a along with significant amounts of hydrolysis product (aniline).
  • 25
    • 34249782153 scopus 로고    scopus 로고
    • The use of 1:1 and 2:1 mixtures of solvents including toluene, xylene, and tetramethylene sulfone along with Eaton's reagent resulted in sluggish conversion. The best conversion obtained was 3% after 20 h at 100°C in a 1:1 mixture of toluene and Eaton's reagent.
    • The use of 1:1 and 2:1 mixtures of solvents including toluene, xylene, and tetramethylene sulfone along with Eaton's reagent resulted in sluggish conversion. The best conversion obtained was 3% after 20 h at 100°C in a 1:1 mixture of toluene and Eaton's reagent.
  • 26
    • 34249828385 scopus 로고    scopus 로고
    • See the Experimental Section
    • See the Experimental Section.
  • 33
    • 34249793866 scopus 로고    scopus 로고
    • Aryl amines with electron donating as well as withdrawing substituents at the meta position resulted in messy reaction profiles. An attempt to synthesize 1,4-dihydro-7-methoxy-4-oxo-2-quinolonecarboxylic acid, methyl ester from a substrate that was derived from O-methoxyaniline afforded only 30% of one major cyclized product with several unidentified side products LC/MS studies
    • Aryl amines with electron donating as well as withdrawing substituents at the meta position resulted in messy reaction profiles. An attempt to synthesize 1,4-dihydro-7-methoxy-4-oxo-2-quinolonecarboxylic acid, methyl ester from a substrate that was derived from O-methoxyaniline afforded only 30% of one major cyclized product with several unidentified side products (LC/MS studies).
  • 36
    • 34249829484 scopus 로고    scopus 로고
    • 2 substituent was only 3% over the same period.
    • 2 substituent was only 3% over the same period.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.