메뉴 건너뛰기




Volumn 73, Issue 21, 2008, Pages 8619-8622

Et3N-induced demethylation-annulation of 3-alkynyl-4-methoxy-2- pyridones and structurally related compounds in the synthesis of furan-fused heterocycles

Author keywords

[No Author keywords available]

Indexed keywords

KETONES;

EID: 55249093394     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8014038     Document Type: Article
Times cited : (66)

References (52)
  • 1
    • 33747152824 scopus 로고    scopus 로고
    • For recent illustrations, see the following reviews:a
    • For recent illustrations, see the following reviews:(a) McGuigan, C.; Balzarini, J. Antiviral Res. 2006, 71, 149.
    • (2006) Antiviral Res , vol.71 , pp. 149
    • McGuigan, C.1    Balzarini, J.2
  • 17
    • 0013567167 scopus 로고    scopus 로고
    • For general reviews on dealkylation of ethers, see:a
    • For general reviews on dealkylation of ethers, see:(a) Ranu, B. C.; Bhar, S. Org. Prep. Proced. Int. 1996, 28, 371.
    • (1996) Org. Prep. Proced. Int , vol.28 , pp. 371
    • Ranu, B.C.1    Bhar, S.2
  • 21
    • 0030446401 scopus 로고    scopus 로고
    • 2-Alkynylphenols are known to undergo facile cycloisomerization under alkaline conditions. For a leading reference, see: Arcadi, A.; Cacchi, S.; Del Rosario, M.; Fabrizi, G.; Marinelli, F. J. Org. Chem. 1996, 61, 9280.
    • 2-Alkynylphenols are known to undergo facile cycloisomerization under alkaline conditions. For a leading reference, see: Arcadi, A.; Cacchi, S.; Del Rosario, M.; Fabrizi, G.; Marinelli, F. J. Org. Chem. 1996, 61, 9280.
  • 23
    • 4444283259 scopus 로고    scopus 로고
    • The related, naturally occurring 7-phenyldihydrofuro[3,2-c] pyridin-4-ones have been the focus of recent attention:(a) Snider, B. B.; Che, G Org. Lett. 2004, 6, 2877.
    • The related, naturally occurring 7-phenyldihydrofuro[3,2-c] pyridin-4-ones have been the focus of recent attention:(a) Snider, B. B.; Che, G Org. Lett. 2004, 6, 2877.
  • 25
    • 55249124121 scopus 로고    scopus 로고
    • So far, only one example of a similar process has been reported in the literature which refers to the formation in low yield of a furo[3,2-c] quinolin-4-one during the reaction of a 3-bromo-4-methoxyquinolin-2-one with a copper acetylide: Gaston, J. L.; Greer, R. J.; Grundon, M. F. J. Chem. Res., Synop. 1985, 135.
    • So far, only one example of a similar process has been reported in the literature which refers to the formation in low yield of a furo[3,2-c] quinolin-4-one during the reaction of a 3-bromo-4-methoxyquinolin-2-one with a copper acetylide: Gaston, J. L.; Greer, R. J.; Grundon, M. F. J. Chem. Res., Synop. 1985, 135.
  • 26
    • 55249102775 scopus 로고    scopus 로고
    • The coupling reaction is normally achieved in less than 16 h at 60°C to give 4a in up to 81% isolated yield.
    • The coupling reaction is normally achieved in less than 16 h at 60°C to give 4a in up to 81% isolated yield.
  • 27
    • 55249123230 scopus 로고    scopus 로고
    • 3N/DMF (2:1) was submitted to microwave irradiation (CEM Discover apparatus; settings 120°C, 150W) during 6 h to give the corresponding furan derivative 3b in 81% isolated yield.
    • 3N/DMF (2:1) was submitted to microwave irradiation (CEM Discover apparatus; settings 120°C, 150W) during 6 h to give the corresponding furan derivative 3b in 81% isolated yield.
  • 28
    • 55249087726 scopus 로고    scopus 로고
    • The slow convertion rate may be explained by increased steric hindrance around the methoxy group
    • The slow convertion rate may be explained by increased steric hindrance around the methoxy group.
  • 29
    • 55249087057 scopus 로고    scopus 로고
    • See Supporting information
    • See Supporting information.
  • 31
    • 33845183073 scopus 로고
    • For a more recent leading reference, see: b
    • For a more recent leading reference, see: (b) Strauss, M.; Torres, R. J. Org. Chem. 1989, 54, 756.
    • (1989) J. Org. Chem , vol.54 , pp. 756
    • Strauss, M.1    Torres, R.2
  • 32
    • 0034048676 scopus 로고    scopus 로고
    • Scarce examples of nucleophilic O-dealkylations have also been reported to occur in the presence of primary and secondary aliphatic amines under high reaction temperatures (150-200°C, a) Nishioka, H, Nagasawa, M, Yoshida, K. Synthesis 2000, 243
    • Scarce examples of nucleophilic O-dealkylations have also been reported to occur in the presence of primary and secondary aliphatic amines under high reaction temperatures (150-200°C):(a) Nishioka, H.; Nagasawa, M.; Yoshida, K. Synthesis 2000, 243.
  • 34
    • 33846064670 scopus 로고    scopus 로고
    • Protonation may occur spontaneously due to the probable presence of water as contaminant in the system or during workup. When used as solvent, MeCN may also intervene as a proton source owing to the predictable high basicity of the furan 2-anion:Shen, K, Fu, Y, Li, J.-N, Liu, L, Guo, Q.-X. Tetrahedron 2007, 63, 1568
    • Protonation may occur spontaneously due to the probable presence of water as contaminant in the system or during workup. When used as solvent, MeCN may also intervene as a proton source owing to the predictable high basicity of the furan 2-anion:Shen, K.; Fu, Y.; Li, J.-N.; Liu, L.; Guo, Q.-X. Tetrahedron 2007, 63, 1568.
  • 35
    • 0141630849 scopus 로고    scopus 로고
    • Previous investigations from the same laboratories have demonstrated the selective synthesis of furopyridones of type 11 through electrophilic annulation/dealkylation reactions of 4-alkoxy-3-alkynyl-2-pyridones:(a) Bossharth, E, Desbordes, P, Monteiro, N, Balme, G Org. Lett. 2003, 5, 2441
    • Previous investigations from the same laboratories have demonstrated the selective synthesis of furopyridones of type 11 through electrophilic annulation/dealkylation reactions of 4-alkoxy-3-alkynyl-2-pyridones:(a) Bossharth, E.; Desbordes, P.; Monteiro, N.; Balme, G Org. Lett. 2003, 5, 2441.
  • 38
    • 33947545753 scopus 로고    scopus 로고
    • This structure is rather uncommon but may be found in natural products: (a) Wang, Y, Shang, X.-Y, Wang, S.-J, Mo, S.-Y, Li, S, Yang, Y.-C, Ye, F, Shi, J.-G, He, L. J. Nat. Prod. 2007, 70, 296
    • This structure is rather uncommon but may be found in natural products: (a) Wang, Y.; Shang, X.-Y.; Wang, S.-J.; Mo, S.-Y.; Li, S.; Yang, Y.-C.; Ye, F.; Shi, J.-G.; He, L. J. Nat. Prod. 2007, 70, 296.
  • 40
    • 33645080180 scopus 로고    scopus 로고
    • Furocoumarins:(a) Wang, X.; Nakagawa-Goto, K.; Kozuka, M.; Tokuda, H.; Nishino, H.; Lee, K.-H. Pharm. Biol. 2006, 44, 116.
    • Furocoumarins:(a) Wang, X.; Nakagawa-Goto, K.; Kozuka, M.; Tokuda, H.; Nishino, H.; Lee, K.-H. Pharm. Biol. 2006, 44, 116.
  • 42
    • 16644367430 scopus 로고    scopus 로고
    • Dihydrofurocoumarins: (c) Motai, T.; Kitanaka, S. Chem. Pharm. Bull. 2004, 52, 1215.
    • Dihydrofurocoumarins: (c) Motai, T.; Kitanaka, S. Chem. Pharm. Bull. 2004, 52, 1215.
  • 46
    • 0037128463 scopus 로고    scopus 로고
    • In many cases, mixtures of isomeric furo[3,2-c]coumarins and furo[3,2-b]chromones have been previously obtained:(a) Lee, Y. R.; Suk, J. Y. Tetrahedron 2002, 58, 2359.
    • In many cases, mixtures of isomeric furo[3,2-c]coumarins and furo[3,2-b]chromones have been previously obtained:(a) Lee, Y. R.; Suk, J. Y. Tetrahedron 2002, 58, 2359.
  • 51
    • 34547603562 scopus 로고    scopus 로고
    • For a recent, selective approach to furo[3,2-c]coumarins, see: (f) Cheng, G.; Hu, Y. Chem. Commun. 2007, 3285.
    • For a recent, selective approach to furo[3,2-c]coumarins, see: (f) Cheng, G.; Hu, Y. Chem. Commun. 2007, 3285.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.