Abstract
Starting from 3-(2,2-dimethyltetrahydro-2H-pyran-4-yl)-2-thioxo-2,3-dihydro-1H-spiro(benzo[h]quinazoline-5,1'-cycloheptan)-4(6H)-one, a series of dibenzo[h]quinazolines was synthesized, in which the spiro(benzo[h]quinazoline-5,1'-cycloheptan)-4(6H)-one moiety in the second position of the –SCH2-group is linked to benzo[h]quinazolines of various structures (spirocyclic and non-spirocyclic). 2-Thioxobenzo[h]quinazoline was converted to a 2-hydrazinyl derivative, whose base-catalyzed hydrazinolysis led to 3-(2,2-dimethyltetrahydro-2H-pyran-4-yl)-3H-spiro(benzo[h]quinazoline-5,1'-cycloheptan)-4(6H)-one. 2-Hydrazinylbenzo[h]quinazoline was reacted with acetone, benzaldehyde, and benzoyl isothiocyanate to obtain hydrazones and thiosemicarbazide. Methods for the synthesis of 4-(2,2-dimethyltetrahydro-2H-pyran-4-yl)-4H-spiro(benzo[h][1,2,4]triazolo[4,3-a]quinazoline-6,1'-cycloheptan)-5(7H)-one and 4-(2,2-dimethyltetrahydro-2H-pyran-4-yl)-1-sulfanyl-4H-spiro(benzo[h][1,2,4]triazolo[4,3-a]quinazoline-6,1'-cycloheptan)-5(7H)-one were developed. Alkylation of the latter gave 1-sulfanyl-substituted 4-(2,2-dimethyltetrahydro-2H-pyran-4-yl)-4H-spiro(benzo[h][1,2,4]triazolo[4,3-a]quinazoline-6,1'-cycloheptan)-5(7H)-ones.
Similar content being viewed by others
REFERENCES
Maurya, H.K., Hasanain, M., Singh, S., Sarkar, J., Dubey, V., Shukla, A., Luqman, S., Khanc, F., and Gupta, A., RSC Adv., 2016, vol. 22, p. 18607.
Wu, L. and Zhang, Ch., RSC Adv., 2016, vol. 34, p. 287555. https://doi.org/10.1039/C6RA03323G
Keshari, A.K., Singh, A.K., Raj, V., Rai, A., Trivedi, P., Ghosh, B., Kumar, U., Rawat, A., Kumar, D., and Saha, S., Drug Des. Devel. Ther., 2017, vol. 11, p. 1623. https://doi.org/10.2147/DDDT.S136692
Sati, N., Kumar, S., and Rawat, M.S., Ind. J. Pharm. Sci., 2009, vol. 71, p. 572.
Sahoo, M., Jena, L., Daf, S., and Kumar, S., Genomics Inform., 2016, vol. 14, p. 104. https://doi.org/10.5808/GI.2016.14.3.104
Gomha, S.M., Abbas, E.M.H., and Farghaly, T., J. Het. Chem., 2017, vol. 54, p. 610. https://doi.org/10.1002/jhet.2632
Maurya, H.K., Verma, R., Alam, S., Pandey, Sh., Pathak, V., Harma, S., Srivastava, K.K., Neg, A.S., and Gupta, A., Bioorg Med. Chem. Lett., 2013, vol. 23, p. 5844. https://doi.org/10.1016/j.bmcl.2013.08.101
Ebied, M.Y., Zaghary, W.A., Amin, K.M., and Hammad, Sh.F., J. Adv. Pharm. Res., 2017, vol. 1, p. 216. https://doi.org/10.21608/aprh.2017.4043
Markosyan, A.I., Hakopyan, Kh.S., Ayvazyan, A.S., Mamyan, S.S., Ayvazyan, A.G., Tamazyan, R.A., Arsenyan, F.H., and Avakimyan, J.A., Chem. J. Armenia, 2018, vol. 71, p. 596.
Markosyan, A.I., Hayrapetyan, K.K., Gabrielyan, S.H., Shirinyan, V.Z., Mamyan, S.S., Avakimyan, J.A., and Stepayan, G.M., Russ. J. Org. Chem., 2018, vol. 54, p. 606. https://doi.org/10.1134/S1070428018040152
Markosyan, A.I., Dilanyan, S.V., Sukasyan, R.S., Arsenyan, F.G., and Garibdzhaanyan, B.T., Pharm. Chem. J., 2008, vol. 42, p. 118. https://doi.org/10.1007/s11094-008-0079-9
Markosyan, A.I., Oganisyan, M.G., Kuroyan, R.A., and Grigoryan, R.T., Arm. Khim. Zh., 1992, vol. 45, p. 208.
Markosyan, A.I., Ayvazyan, A.S., Gabrielyan, S.H., Mamyan, S.S., Arsenyan, F.H., Safaryan, A.S., and Arakelyan, H.H., Pharm. Chem. J., 2021, vol. 55, p. 133. https://doi.org/10.1007/s11094-021-02392-2
Markosyan, A.I., Ayvazyan, A.S., Gabrielyan, S.A., and Mamyan, S.S., Russ. J. Org. Chem., 2021, vol. 57, p. 383. https://doi.org/10.1134/S107042802103009X
Rukovodstvo po provedeniyu doklinicheskikh issledovanii lekarstvennykh sredstv (Guidelines for Conducting Preclinical Studies of Drugs), Mironov, A.N., Ed., Moscow: Meditsina, 2012.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare no conflict of interest.
Rights and permissions
About this article
Cite this article
Markosyan, A.I., Ayvazyan, A.S., Gabrielyan, S.H. et al. Some Transformations of 3-(2,2-Dimethyltetrahydro-2H-pyran-4-yl-2-thioxo-2,3-dihydro-1H-spiro(benzo[h]quinazoline-5,1'-cycloheptan)-4(6H)-one. Russ J Org Chem 58, 200–208 (2022). https://doi.org/10.1134/S1070428022020075
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428022020075