Abstract
Interaction of 1-(oxiran-2-ylmethyl)-1H-indole-3-carboxaldehyde with primary amines occurs at oxirane moiety and leads to b-aminoalcohols. Quantum-chemical calculations show that these products are more stable than possible alternative Schiff bases arising from aldehyde group of the considered bielectrophiles.
References
1.
10.1016/j.mencom.2011.07.021_bib0005
Bucourt
Bull. Soc. Chim. Fr.,
1961
2.
Noland W.E., Christensen G.M., Sauer G.L., Dutton G.G.
Journal of the American Chemical Society,
1955
3.
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, V. Bakken, 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 and J. A. Pople, Gaussian 03, Gaussian Inc., Wallingford CT, 2004.
4.
Parr R.G., Szentpály L.V., Liu S.
Journal of the American Chemical Society,
1999
5.
10.1016/j.mencom.2011.07.021_bib0025
Albert
Ionization Constants of Acids and Bases: a Laboratory Manual,
1962
6.
Bergero F., Alvaro C.E., Nudelman N.S., Ramos de Debiaggi S.
Journal of Molecular Structure THEOCHEM,
2009