Abstract
Protonation and methylation of 5-oxo-7,12-dihydro-5H-isoquino[2,3-a]quinazoline occur at the N(6) atom, while methylation of 5-oxo- and 6-methyl-5-oxo-6,6a,7,12-tetrahydro-5H-isoquino[2,3-a]quinazolines takes place at the N(13) atom; the degree of stereoselectivity varies depending on the presence of a substituent attached to N(13). Based on PMR spectral analysis utilizing the nuclear Overhauser effect, we have established the structure and studied the conformational behavior of the tosylate derivatives of cis-13-methyl-, trans-13-methyl-, and cis-6,13-dimethyl-5-oxo-6,6a,7-12-tetrahydro-5H-isoquino[2,3-a]quinazolinium ions.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature Cited
V. N. Kisel', V. A. Kovtunenko, A. V. Turov, A. K. Tyltin, and F. S. Babichev, Dokl. Akad. Nauk SSSR, 306, 628 (1989).
T. Williamson, in: Chemistry of Quinazoline, Heterocyclic Compounds, R. Alderfield (ed.) [Russian translation], IL, Moscow (1960).
R. Günther, Introduction to NMR Spectroscopy [in Russian], Mir, Moscow (1984).
C. A. G. Haasnoot, F. A. A. M. Leeuw, and C. Altona, Tetrahedron, 36, 2783 (1980).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 389–394, March 1991,
Rights and permissions
About this article
Cite this article
Kisel', V.M., Kovtunenko, V.A., Turov, A.V. et al. Alkylation and reduction reactions in the isoquino[2,3-a]quinazoline series. Chem Heterocycl Compd 27, 316–321 (1991). https://doi.org/10.1007/BF00474239
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00474239