A simple approach to multifunctionalized N1-alkylated 7-amino-6-azaoxindole derivatives using their in situ stabilized tautomer form

Tzvetkov NT, Neumann B, Stammler H-G, Antonov L (2016)
TETRAHEDRON 72(41): 6455-6466.

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A simple approach for the synthesis of multifunctionalized N1-alkyl 7-amino-6-azaoxindole derivatives was developed and investigated. Formation of 5-amino- and 7-amino-6-aza-2-oxindoles 12a and 13a, respectively, was achieved using an intramolecular reductive cyclization as a key step. Subsequent alkylation of the pyrrole N1 atom in 12a led to the desired N1-alkylated compounds 22a-24 comprising different functionalities. Alkylation of 5-amino-substituted regioisomer 13a under the same conditions as used for 12a did not resulted in N1-alkylated products. To find a plausible explanation for the observed differences in reactivity, we investigated the possible tautomers of 12a and 13a and the distribution of their neutral and ionized forms in a gas phase. The relevant physicochemical properties of compounds 12a and 23 were determined. (C) 2016 Elsevier Ltd. All rights reserved.
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Tzvetkov NT, Neumann B, Stammler H-G, Antonov L. A simple approach to multifunctionalized N1-alkylated 7-amino-6-azaoxindole derivatives using their in situ stabilized tautomer form. TETRAHEDRON. 2016;72(41):6455-6466.
Tzvetkov, N. T., Neumann, B., Stammler, H. - G., & Antonov, L. (2016). A simple approach to multifunctionalized N1-alkylated 7-amino-6-azaoxindole derivatives using their in situ stabilized tautomer form. TETRAHEDRON, 72(41), 6455-6466. doi:10.1016/j.tet.2016.08.055
Tzvetkov, N. T., Neumann, B., Stammler, H. - G., and Antonov, L. (2016). A simple approach to multifunctionalized N1-alkylated 7-amino-6-azaoxindole derivatives using their in situ stabilized tautomer form. TETRAHEDRON 72, 6455-6466.
Tzvetkov, N.T., et al., 2016. A simple approach to multifunctionalized N1-alkylated 7-amino-6-azaoxindole derivatives using their in situ stabilized tautomer form. TETRAHEDRON, 72(41), p 6455-6466.
N.T. Tzvetkov, et al., “A simple approach to multifunctionalized N1-alkylated 7-amino-6-azaoxindole derivatives using their in situ stabilized tautomer form”, TETRAHEDRON, vol. 72, 2016, pp. 6455-6466.
Tzvetkov, N.T., Neumann, B., Stammler, H.-G., Antonov, L.: A simple approach to multifunctionalized N1-alkylated 7-amino-6-azaoxindole derivatives using their in situ stabilized tautomer form. TETRAHEDRON. 72, 6455-6466 (2016).
Tzvetkov, Nikolay T., Neumann, Beate, Stammler, Hans-Georg, and Antonov, Liudmil. “A simple approach to multifunctionalized N1-alkylated 7-amino-6-azaoxindole derivatives using their in situ stabilized tautomer form”. TETRAHEDRON 72.41 (2016): 6455-6466.
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