New derivatives of dihydroquinazoline[3,2-c][2, 3]benzodiazepin-14(6H)-ones were synthesized using the Pictet-Spengler reaction of 3-amino-2-(3,4-dimethoxybenzyl)quinazolin-4(3H)-one with aliphatic and heterocyclic aldehydes in acid media.
Similar content being viewed by others
References
A. S. Tolkunov, A. I. Khizhan, and S. L. Bogza, Khim. Geterotsikl. Soedin., 745 (2010). [Chem. Heterocycl. Comp., 46, 871 (2010)].
V. I. Dudenko, I. V. Komissarov, A. T. Dolzhenko, and Yu. A. Nikolyukin, β-Carbonyls. Chemistry and Neurobiology [in Russian], Naukova Dumka (1992).
S. V. Tolkunov, in: V. G. Kartsev (editor), Selected Synthetic Methods and Heterocycle Modification [in Russian], vol. 2, IBS-PRESS, Moscow (2003), p. 444.
S. V. Tolkunov and V. Yu. Popov, in: V. G. Kartsev (editor), Selected Synthetic Methods and Heterocycle Modification [in Russian], vol. 5, ICSPF-PRESS, Moscow (2006), p. 123.
E. E. Shults, G. A. Tolstikov, and V. G. Kartsev, in: V. G. Kartsev (editor), Selected Synthetic Methods and Heterocycle Modification [in Russian], vol. 5, ICSPF-PRESS, Moscow (2006), p. 273.
V. A. Tuskaev, in: V. G. Kartsev (editor), Selected Synthetic Methods and Heterocycle Modification [in Russian], vol. 5, ICSPF-PRESS, Moscow (2006), p. 166.
M. Shamma, The Isoquinoline Alcaloids: Chemistry and Pharmacology, in: A. T. Blomquist and H. Wasserman (editors), Organic Chemistry, vol. 25, Academic Press, New York (1972).
E. D. Cox and J. M. Cook, Chem. Rev., 95, 1797 (1995).
S. L. Bogza, K. I. Kobrakov, A. A. Malienko, I. F. Perepichka, S. Yu. Sujkov, M. R. Bruce, S. B. Lyubchik, A. S. Batsanov, and N. M. Bogdan, Org. Biomol. Chem., 3, 932 (2005).
S. Duggineni, D. Sawant, B. Saha, and B. Kundu, Tetrahedron, 62, 3228 (2006).
A. A. Ponomarev, Syntheses and Reactions of Furan Compounds [in Russian], Izd. Saratovsk. Univ., Saratov, Russia (1960), p. 19.
L. I. Belen'kii, in: V. G. Kartsev (editor), Selected Synthetic Methods and Heterocycle Modification [in Russian], vol. 2, IBS-PRESS, Moscow (2003), p. 25.
Author information
Authors and Affiliations
Corresponding author
Additional information
*For Communication 1, see [1].
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 882-893, June, 2010.
Rights and permissions
About this article
Cite this article
Tolkunov, A.S., Bogza, S.L. Pictet-spengler reaction in the synthesis of condensed benzodiazepines. 2.* Synthesis of new derivatives of 11,12-dihydroquinazoline-[3,2-c][2, 3]benzodiazepin-14(6H)-ones. Chem Heterocycl Comp 46, 711–720 (2010). https://doi.org/10.1007/s10593-010-0573-3
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-010-0573-3