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Volumn 9, Issue 6, 2007, Pages 1041-1045

A library of 3-aryl-4,5-dihydroisoxazole-5-carboxamides

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; ISOXAZOLE DERIVATIVE;

EID: 36649000038     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc700117a     Document Type: Article
Times cited : (20)

References (30)
  • 6
    • 36649011295 scopus 로고    scopus 로고
    • U.S. Patent 5 716 967
    • (b) Kleinman, E. F. U.S. Patent 5 716 967, 1998.
    • (1998)
    • Kleinman, E.F.1
  • 7
  • 21
    • 0003463148 scopus 로고    scopus 로고
    • 3rd ed, Greene, T. W, Wuts, P. G. M, John Wiley & Sons: New York
    • Protective Groups in Organic Synthesis, 3rd ed.; Greene, T. W., Wuts, P. G. M.; John Wiley & Sons: New York, 1999; p 355.
    • (1999) Protective Groups in Organic Synthesis , pp. 355
  • 22
    • 36649026582 scopus 로고    scopus 로고
    • The dipole-LUMO-dipolarophile-HOMO energy gaps (given over the solid arrows in Figure 4) are option A (0.420 eV, methyl propiolate, option B (0.413 eV, N-methylpropiolamide, option C (0.373 eV, N-methylacrylamide, and option D (0.395 eV, methyl acrylate, The dipole-HOMO-dipolarophile-LUMO energy gaps, given parenthetically over the dashed arrows in Figure 4, are all larger than the dipole-LUMO-dipolarophile- HOMO energy gaps. That said, there are subtle differences between the calculated HOMO-LUMO energy gaps that are dominating the dipole-dipolarophile interactions, b) For all the other HOMOs observed for the dipolarophiles, the alkene or alkyne is not conjugated into the carbonyl. For comparative consistency, a molecular orbital where the alkyne is not conjugated into the carbonyl was located at HOMO-1. Regardless of whether the system utilizes the HOMO or HOMO-1, the dipole-LUMO-dipolarophile-HOMO interaction still has a smaller energy gap tha
    • (a) The dipole-LUMO-dipolarophile-HOMO energy gaps (given over the solid arrows in Figure 4) are option A (0.420 eV, methyl propiolate); option B (0.413 eV, N-methylpropiolamide); option C (0.373 eV, N-methylacrylamide); and option D (0.395 eV, methyl acrylate). The dipole-HOMO-dipolarophile-LUMO energy gaps, given parenthetically over the dashed arrows in Figure 4, are all larger than the dipole-LUMO-dipolarophile- HOMO energy gaps. That said, there are subtle differences between the calculated HOMO-LUMO energy gaps that are dominating the dipole-dipolarophile interactions. (b) For all the other HOMOs observed for the dipolarophiles, the alkene or alkyne is not conjugated into the carbonyl. For comparative consistency, a molecular orbital where the alkyne is not conjugated into the carbonyl was located at HOMO-1. Regardless of whether the system utilizes the HOMO or HOMO-1, the dipole-LUMO-dipolarophile-HOMO interaction still has a smaller energy gap than the dipole-HOMO-dipolarophile-LUMO interaction.
  • 23
    • 0032567968 scopus 로고    scopus 로고
    • A nice solid phase synthesis of 3-substituted 4,5-dihydroisoxazole-5- carboxylic acids 12 has been reported. See: Cheng, J. P.; Mjalli, A. M. M. Tetrahedron Lett. 1998, 39, 939.
    • A nice solid phase synthesis of 3-substituted 4,5-dihydroisoxazole-5- carboxylic acids 12 has been reported. See: Cheng, J. P.; Mjalli, A. M. M. Tetrahedron Lett. 1998, 39, 939.
  • 30
    • 36649035184 scopus 로고    scopus 로고
    • 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. I, 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
    • 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. I.; 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. and Pople, J. A. GAUSSIAN03, revision B.04; Gaussian, Inc.: Pittsburgh, PA, 2003.


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