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Volumn 50, Issue 26, 2009, Pages 3628-3630

A new entry to α-alkylidene-β-lactams by 4-exo-dig cyclization of carbamoyl radicals

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; BETA LACTAM DERIVATIVE; CARBON; NITROGEN; RADICAL; SELENIUM DERIVATIVE; TELLURIUM; VINYL DERIVATIVE;

EID: 65549108043     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.03.071     Document Type: Article
Times cited : (25)

References (83)
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    • note
    • Cyclization did not proceed when the reaction was carried out at 80 °C.
  • 54
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    • Walton and co-workers also examined 4-exo-dig cyclization of carbamoyl radical generation from N-benzyl-N-alkynyl-(1-methyl)cyclohexa-2,5-diene-1-carboxamide, at 80 °C and mentioned that the only product isolated was formamide. However, the GC-MS chromatogram showed a small amount of α-alkylidene-β-lactam, although this was not confirmed by isolation and NMR spectral characterisation, see:
    • Walton and co-workers also examined 4-exo-dig cyclization of carbamoyl radical generation from N-benzyl-N-alkynyl-(1-methyl)cyclohexa-2,5-diene-1-carboxamide, at 80 °C and mentioned that the only product isolated was formamide. However, the GC-MS chromatogram showed a small amount of α-alkylidene-β-lactam, although this was not confirmed by isolation and NMR spectral characterisation, see:. Bella A.F., Jackson L.V., and Walton J.C. Org. Biomol. Chem. 2 (2004) 421
    • (2004) Org. Biomol. Chem. , vol.2 , pp. 421
    • Bella, A.F.1    Jackson, L.V.2    Walton, J.C.3
  • 55
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    • note
    • Carbamotelluroates 5 were completely comsumed in all runs. Complex mixtures were obtained and five-membered lactams were not detected except run 7.
  • 59
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    • For theoretical and experimental studies of 5-endo-dig cyclization:
    • For theoretical and experimental studies of 5-endo-dig cyclization:. Alabugin I.V., and Manoharan M. J. Am. Chem. Soc. 127 (2005) 9535
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 9535
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    • For 5-endo-dig cyclization of heteroatom-centered radicals:
    • For 5-endo-dig cyclization of heteroatom-centered radicals:. Bartan T.J., and Groh B.L. J. Org. Chem. 50 (1985) 158
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    • Bartan, T.J.1    Groh, B.L.2
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    • Frisch, M. J, Trucks, G. W, Schlegel, H. B, Scuseria, G. E, Robb, M. A, Cheeseman, J. R, Montgomery, J. A. Jr, Vreven, T, Kudin, K. N, Burant, J. C, Millam, J. M, Iyengar, S. S, Tomasi, J, Barone, V, Mennucci, B, Cossi, M, Scalmani, G, Rega, N, Petersson, G. A, Nakatsuji, H, Hada, M, Ehara, M, Toyota, K, Fukuda, R, Hasegawa, J, Ishida, M, Nakajima, T, Honda, Y, Kitao, O, Nakai, H, Klene, M, Li, X, Knox, J. E, Hratchian, H. P, Cross, J. B, Adamo, C, Jaramillo, J, Gomperts, R, Stratmann, R. E, Yazyev, O, Austin, A. J, Cammi, R, Pomelli, C, Ochterski, J. W, Ayala, P. Y, Morokuma, K, Voth, G. A, Salvador, P, Dannenberg, J. J, Zakrzewski, V. G, Dapprich, S, Daniels, A. D, Strain, M. C, Farkas, O, Malick, D. K, Rabuck, A. D, Raghavachari, K, Foresman, J. B, Ortiz, J. V, Cui, Q, Baboul, A. G, Clifford, S, Cioslowski, J, Stefanov, B. B, Liu, G, Liashenko, A, Piskorz, P, Komaromi, I, Martin, R. L, Fox, D. J, Keith, T, Al-Lah
    • Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A. Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. gaussian 03, Revision B.01, Gaussian, Pittsburgh PA, 2003.
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    • note
    • 4), respectively, and found to be almost the same as that of Ab to Bb.
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    • ref. 14
    • ref. 14.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.