Biogenetically inspired synthesis of marine C6N4 2-aminoimidazole alkaloids: Ab initio calculations, tautomerism, and reactivity

Organic Letters

Volumn 6, Issue 22, 2004, Pages 3933-3936

  Abou Jneid, Robert ^a   Ghoulami, Said ^a   Martin, Marie Thérèse ^a   Dau, Elise Tran Huu ^a   Travert, Nathalie ^a   Al Mourabit, Ali ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID DERIVATIVE; IMIDAZOLE DERIVATIVE;

AB INITIO CALCULATION; ADDITION REACTION; ARTICLE; BIOGENESIS; ENERGY TRANSFER; SUBSTITUTION REACTION; SYNTHESIS;

EID: 8744318421     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048529e     Document Type: Article

References (26)

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21. Total energies of the four tautomers I-IV of 1 were performed with ab initio calculations using the Gaussian 98 program (see ref 14a). All the structures were optimized with gradient techniques using the 6-316* basis set, which includes one orbital polarization function on C and N (see ref 14b): (a) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98; Gaussian, Inc.: Pittsburgh, PA, 1998. (b) Hariaran, P. C.; Pople, J. A. Theor. Chim. Acta. 1973, 28, 213-222.
22. Total energies of the four tautomers I-IV of 1 were performed with ab initio calculations using the Gaussian 98 program (see ref 14a). All the structures were optimized with gradient techniques using the 6-316* basis set, which includes one orbital polarization function on C and N (see ref 14b): (a) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98; Gaussian, Inc.: Pittsburgh, PA, 1998. (b) Hariaran, P. C.; Pople, J. A. Theor. Chim. Acta. 1973, 28, 213-222.
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24. For isomerization-deuteration, see also: (a) Lindel, T.; Hochgürtel, M. J. Org. Chem. 2000, 65, 2806-2809. (b) Daninos-Zeghal, S.; Al-Mourabit, A.; Ahond, A.; Poupat, C.; Potier, P. Tetrahedron 1997, 53, 7605-7614.
25. For isomerization-deuteration, see also: (a) Lindel, T.; Hochgürtel, M. J. Org. Chem. 2000, 65, 2806-2809. (b) Daninos-Zeghal, S.; Al-Mourabit, A.; Ahond, A.; Poupat, C.; Potier, P. Tetrahedron 1997, 53, 7605-7614.
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