![Diastereoselective synthesis of chromeno[4,3-d]pyrimidines](/upload/12631c5e396938a702bdd516ae8c4208/issues/cover/aeeadbe79f068d9885fba8f04ac27a3b.png)
from 01.01.2023 until now
Yaroslavl State Technical University
from 01.01.2018 to 01.01.2023
Yaroslavl, Yaroslavl, Russian Federation
Yaroslavl, Yaroslavl, Russian Federation
Yaroslavl, Yaroslavl, Russian Federation
UDK 547.853.3 Пиримидин
The paper investigates the diastereoselective synthesis of chromeno[4,3-d]pyrimidines by isolation and cyclization of diastereomerically pure dihydropyrimidine addition intermediates to resorcinol. The authors discovered the reversibility of the addition reaction to be an important factor that could neutralize the dominant formation of one of the intermediate diastereomers.
hexahydrochromeno[4,3-d]pyrimidines, resorcinol, acid-catalyzed condensation, diastereoselectivity
1. Heravi, M.M., Moradi, R., Mohammadkhani, L. & Moradi, B. (2018) Current progress in asymmetric Biginelli reaction: an update, Mol. Diversity, (22), pp. 751-767. DOI:https://doi.org/10.1007/s11030-018-9841-4 [online]. Availa-ble at: https://link.springer.com/article/10.1007/s11030-018-9841-4 (accessed 14.02.2023).
2. Dalpozzo, R. & Mancuso, R. (2019) Recent advances in organocatalyzed asymmetric synthesis of benzopyran and benzodihydropyran (chromane) nuclei, Symmetry, 11(12), pp. 1510. DOI:https://doi.org/10.3390/sym11121510 [online]. Available at: https://www.mdpi.com/2073-8994/11/12/1510
3. Shen, H.C. (2009) Asymmetric synthesis of chiral chromans, Tetrahedron, (65), pp. 3931-3952. DOI:https://doi.org/10.1016/j.tet.2009.02.002.
4. Hang, Z., Zhu, J., Lian, X., Xu, P., Yu, H. & Han, S. (2016) A highly enantioselective Biginelli reaction using self-assembled methanoproline–thiourea organocatalysts: asymmetric synthesis of 6-isopropyl-3,4-dihydropyrimidines, Chem. Commun., 52(1), pp. 80-83. DOI:https://doi.org/10.1039/C5CC07880F [online]. Available at: https://pubs.rsc.org/en/content/articlehtml/2015/cc/c5cc07880f (accessed 14.02.2023).
5. Debonis, S., Simorre, J.P., Crevel, I., Lebeau, L., Skoufias, D.A., Blangy, A., Ebel, C., Gans, P., Cross, R., Hackney, D.D., Wade, R.H. & Kozielski, F. (2003) Interaction of the mitotic inhibitor monastrol with human kinesin Eg5, Biochemistry, 42(2), pp. 338–349. DOI:https://doi.org/10.1021/bi026716j [online]. Available at: https://pubs.acs.org/doi/abs/10.1021/bi026716j
6. Gong, L. Z., Chen, X.H. & Xu, X.Y. (2007) Asymmetric organocatalytic Biginelli reactions: a new approach to quickly access optically active 3,4-dihydropyrimidin-2-(1H)-ones, Chem. - Eur. J., 13(32), pp. 8920-8926. DOI:https://doi.org/10.1002/chem.200700840 [online]. Available at: https://chemistry-europe.onlinelibrary.wiley.com/doi/full /10.1002/chem.200700840 (accessed 14.02.2023).
7. Zu, L., Zhang, S., Xie, H. & Wang, W. (2009) Catalytic asymmetric oxa-Michael-Michael cascade for facile construction of chiral chromans via an aminal intermediate, Org. Lett., 11(7), pp. 1627-1630.
8. Yu, H., Xu, P., He, H., Zhu, J., Lin, H. & Han, S. (2017) Highly enantioselective Biginelli reactions using methanopyroline/thiourea–based dual organocatalyst systems: asymmetric synthesis of 4-substituted unsaturated aryl dihydropyrimidines, Tetrahedron: Asymmetry, 28(2), pp. 257-265.
9. Hu, N., Li, K., Wang, Z. & Tang, W. (2016) Synthesis of chiral 1,4-benzodioxanes and chromans by enantioselective palladium-catalyzed alkene aryloxyarylation reactions, Angew. Chem., Int. Ed., 55(16), pp. 5044 5048.
10. Filimonov, S.I., Chirkova, Zh.V., Kabanova, M.V., Makarova, E.S., Shetnev, A.A., Panova, V.A. & Suponitsky, K.Yu. (2019) A condensation of Biginelli products with 1,3-benzenediols: a facile access to diastereomerically pure hexahydro-5H-chromeno[4,3-d]pyrimidin-5-ones, ChemistrySelect., 4(33), pp. 9550 9555. DOI:https://doi.org/10.1002/slct.201901997 [online]. Available at: https://chemistry-europe.onlinelibrary. wiley.com/doi/10.1002/slct.201901997
11. Makarova, E.S., Kabanova, M.V., Filimonov, S.I., Shetnev, A.A. & Suponitsky, K.Yu. (2022) Synthesis and modification by hydroxyl group of substituted hexahydro-2H-chromeno[4,3-d]pyrimidin-2,5-diones, Izv. AN. Ser. khim., (5), pp. 1034-1042 (in Russian).
12. Filimonov, S.I., Makarova, E.S., Chirkova, J.V. & Kabanova, M.V. (2022) Diastereomeric composition of the reaction of the formation of hexahydro-5H-chromeno[4,3-d]pyrimidin-5-ones, From Chemistry Towards Technology Step-By-Step, 3(1), pp. 68-75 [online]. Available at: http://chemintech.ru/index.php/tor/2022tom3no1(accessed 14.02.2023) (in Russian).
