Nucleophilic behaviour of DBU in a conjugate addition reaction

Tetrahedron Letters

Volumn 38, Issue 40, 1997, Pages 7003-7006

  Johnson, Mary George ^a   Foglesong, Robert J ^a  

^a Sphinx Pharmaceuticals Corporation   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CAPROLACTAM DERIVATIVE; PYRIDONE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; MASS SPECTROMETRY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030801916     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01675-4     Document Type: Article

References (18)

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7. Some other conditions for conversion of pyrones to pyridones: Dobbin, P. S.; Hider, R.C. Venkatramani, L.; Siripitayananon, J.; Van Der Helm, D. J. Heterocyclic Chem. 1993, 30, 723-737. Djerrari, B.; Essassi, E.M.; Fifani, J. Bull. Soc. Chim. Belg. 1993, 102, 565-573. Dehmlow, E.V.; Westerheide, R. Heterocycles. 1994, 37, 355-366. Faeber, M.; Osiander, H.; Severin, T. J. Heterocyclic Chem. 1994, 31, 947-956. Markees, D. G. J. Heterocyclic Chem. 1990, 127, 1837-1838.
8. Some other conditions for conversion of pyrones to pyridones: Dobbin, P. S.; Hider, R.C. Venkatramani, L.; Siripitayananon, J.; Van Der Helm, D. J. Heterocyclic Chem. 1993, 30, 723-737. Djerrari, B.; Essassi, E.M.; Fifani, J. Bull. Soc. Chim. Belg. 1993, 102, 565-573. Dehmlow, E.V.; Westerheide, R. Heterocycles. 1994, 37, 355-366. Faeber, M.; Osiander, H.; Severin, T. J. Heterocyclic Chem. 1994, 31, 947-956. Markees, D. G. J. Heterocyclic Chem. 1990, 127, 1837-1838.
9. Some other conditions for conversion of pyrones to pyridones: Dobbin, P. S.; Hider, R.C. Venkatramani, L.; Siripitayananon, J.; Van Der Helm, D. J. Heterocyclic Chem. 1993, 30, 723-737. Djerrari, B.; Essassi, E.M.; Fifani, J. Bull. Soc. Chim. Belg. 1993, 102, 565-573. Dehmlow, E.V.; Westerheide, R. Heterocycles. 1994, 37, 355-366. Faeber, M.; Osiander, H.; Severin, T. J. Heterocyclic Chem. 1994, 31, 947-956. Markees, D. G. J. Heterocyclic Chem. 1990, 127, 1837-1838.
10. Some other conditions for conversion of pyrones to pyridones: Dobbin, P. S.; Hider, R.C. Venkatramani, L.; Siripitayananon, J.; Van Der Helm, D. J. Heterocyclic Chem. 1993, 30, 723-737. Djerrari, B.; Essassi, E.M.; Fifani, J. Bull. Soc. Chim. Belg. 1993, 102, 565-573. Dehmlow, E.V.; Westerheide, R. Heterocycles. 1994, 37, 355-366. Faeber, M.; Osiander, H.; Severin, T. J. Heterocyclic Chem. 1994, 31, 947-956. Markees, D. G. J. Heterocyclic Chem. 1990, 127, 1837-1838.
11. Some other conditions for conversion of pyrones to pyridones: Dobbin, P. S.; Hider, R.C. Venkatramani, L.; Siripitayananon, J.; Van Der Helm, D. J. Heterocyclic Chem. 1993, 30, 723-737. Djerrari, B.; Essassi, E.M.; Fifani, J. Bull. Soc. Chim. Belg. 1993, 102, 565-573. Dehmlow, E.V.; Westerheide, R. Heterocycles. 1994, 37, 355-366. Faeber, M.; Osiander, H.; Severin, T. J. Heterocyclic Chem. 1994, 31, 947-956. Markees, D. G. J. Heterocyclic Chem. 1990, 127, 1837-1838.
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16. Lammers, et al obtained the aminocaprolactam 4 via the azafulvene: Lammers, H.; Cohen-Fernandes, P.; Habraken, C.L. Tetrahedron 1994, 50, 865-870. (figure presented)
17. Other workers have investigated the α-alkylations of α,β-unsaturated enones with DBU and DABCO and have concluded that DBU does not catalyze the reaction via a 1,4 addition as is the case with DABCO: Hwu, J. R.; Hakimelahi, G. H.; Chou, C. T. Tetrahedron Lett. 1992, 33, 6469-6472.
18. b) Basavaiah, D.; Gowriswari, V. V. L. Tetrahedron Lett. 1986, 27, 2031-2032.