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Volumn , Issue 24, 2006, Pages 5485-5494

New highly strained multifunctional heterocycles by intramolecular cycloadditions of nitrones to bicyclopropylidene moieties

Author keywords

amino acids; lactams; Cycloaddition; Small ring systems; Spiro compounds; Tetrahydropyridones

Indexed keywords


EID: 33845919314     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600417     Document Type: Article
Times cited : (23)

References (56)
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    • For leading reviews on 1,3-dipolar cycloadditions engaging nitrones, see: a, Ed, A. Padwa, John Wiley & Sons, New York
    • For leading reviews on 1,3-dipolar cycloadditions engaging nitrones, see: a) J. J. Tufariello, in: 1,3-Dipolar Cycloaddition Chemistry (Ed.: A. Padwa), John Wiley & Sons, New York, 1984;
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    • The formation of tricyclic compounds by intramolecular cycloaddition of an in situ formed benzoylhydrazone of a methylenecyclopropyl ketone unit during an attempted synthesis of the corresponding acyclic hydrazone has been observed: L. Patient, M. B. Berry, S. J. Coles, M. B. Hursthouse, J. D. Kilburn, Chem. Commun. 2003, 2552-2553
    • The formation of tricyclic compounds by intramolecular cycloaddition of an in situ formed benzoylhydrazone of a methylenecyclopropyl ketone unit during an attempted synthesis of the corresponding acyclic hydrazone has been observed: L. Patient, M. B. Berry, S. J. Coles, M. B. Hursthouse, J. D. Kilburn, Chem. Commun. 2003, 2552-2553.
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    • All calculations were performed using the Spartan'04 (Spartan'04, Wavefunction Inc, Irvine, CA) and Gaussian 03 program packages: M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Pi
    • All calculations were performed using the Spartan'04 (Spartan'04, Wavefunction Inc., Irvine, CA) and Gaussian 03 program packages: M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian 03, Revision B.04, Gaussian Inc., Pittsburgh PA, 2003. Enthalpies of formation and equilibrium geometries have been obtained from DFT calculations on the B3LYP/6-31G* level of theory with Gaussian. The lowest energy conformer obtained after conformational analysis with Spartan using the MMFF force field was used as the starting geometry.
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    • 1H NMR spectrum of the residue showed inter alia the presence of N- benzylhydroxylamine and (Z)-benzaldoxime in a ca. 1.4:1 ratio (according to the integrals of the signals of methylene protons of N-benzylhydroxylamine and of the oxime proton).
    • 1H NMR spectrum of the residue showed inter alia the presence of N- benzylhydroxylamine and (Z)-benzaldoxime in a ca. 1.4:1 ratio (according to the integrals of the signals of methylene protons of N-benzylhydroxylamine and of the oxime proton).
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    • 2D-NOESY of 28a was carried out with an INOVA-600 spectrometer (H-600 MHz) using the pulse sequence NOESY (spectral width: 2155 Hz, acquisition time: 0.150 s, mixing time Δ, 1 s, relaxation delay: 1.4 s, total acquisition time: 3.42 h, The experiment was run at 25°C with a 0.2 M sample (18 mg in 0.5 mL) in CDCl3;
    • 3;
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    • 6 (same instrument, same sample concentration), in which 7-H protons are better separated, and confirmed the 2D-NOESY results. The automatic pulse sequence NOESY 1D was used (spectral width: 9596 Hz, acquisition time: 3.334 s, mixing time Δ = 0.5 s, relaxation delay: 1.0 s, spin off; line broadening: 0.3 Hz for the processing).
    • 6 (same instrument, same sample concentration), in which 7-H protons are better separated, and confirmed the 2D-NOESY results. The automatic pulse sequence NOESY 1D was used (spectral width: 9596 Hz, acquisition time: 3.334 s, mixing time Δ = 0.5 s, relaxation delay: 1.0 s, spin off; line broadening: 0.3 Hz for the processing).
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.