![Diastereoselective synthesis of chromeno[4,3-d]pyrimidines](/upload/12631c5e396938a702bdd516ae8c4208/issues/cover/aeeadbe79f068d9885fba8f04ac27a3b.png)
graduate student from 01.01.2023 until now
Yaroslavl State Technical University
student from 01.01.2018 to 01.01.2023
Yaroslavl, Yaroslavl, Russian Federation
graduate student
Yaroslavl, Yaroslavl, Russian Federation
Yaroslavl, Yaroslavl, Russian Federation
UDK 547.853.3 Пиримидин
Issledovana diastereonapravlennost' sinteza hromeno[4,3-d]pirimidinov putem vydeleniya i ciklizacii dominiruyuschih diastereomerno chistyh promezhutochnyh produktov prisoedineniya digidropirimidinov k rezorcinu. Ustanovleno, chto vazhnym faktorom yavlyaetsya obratimost' reakcii prisoedineniya, kotoraya mozhet nivelirovat' dominiruyuschee obrazovanie odnogo iz promezhutochnyh diastereomerov
geksagidrohromeno[4,3-d]pirimidinny, rezorcin, kislotno-kataliziruemaya kondensaciya, diastereonapravlennost'
1. Heravi M.M., Moradi R., Mohammadkhani L., Moradi B. Current progress in asymmetric Biginelli reaction: an update // Mol. Diversity. 2018. Vol. 22. P. 751–767. DOI:https://doi.org/10.1007/s11030-018-9841-4. URL: https://link.springer.com/article/10.1007/s11030-018-9841-4
2. Dalpozzo R., Mancuso R. Recent advances in organocatalyzed asymmetric synthesis of benzopyran and benzodihydropyran (chromane) nuclei // Symmetry. 2019. Vol. 11, no. 12. P. 1510. DOI:https://doi.org/10.3390/sym11121510. URL: https://www.mdpi.com/2073-8994/11/12/1510
3. Shen H.C. Asymmetric synthesis of chiral chromans // Tetrahedron. 2009. Vol. 65. P. 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. A highly enantioselective Biginelli reaction using self-assembled methanoproline–thiourea organocatalysts: asymmetric synthesis of 6-isopropyl-3,4-dihydropyrimidines // Chem. Commun. 2016. Vol. 52, no. 1. P. 80-83. DOI:https://doi.org/10.1039/C5CC07880F. URL: https://pubs.rsc.org/en/content/articlehtml/2015/cc/c5cc07880f
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. Interaction of the mitotic inhibitor monastrol with human kinesin Eg5 // Biochemistry. 2003. Vol. 42, no. 2. P. 338–349. DOI:https://doi.org/10.1021/bi026716j. URL: https://pubs.acs.org/doi/abs/10.1021/bi026716j
6. Gong, L.Z., Chen, X.H., Xu, X.Y. Asymmetric organocatalytic Biginelli reactions: a new approach to quickly access optically active 3,4-dihydropyrimidin-2-(1H)-ones // Chem. - Eur. J. 2007. Vol. 13, no. 32. P. 8920 8926. DOI:https://doi.org/10.1002/chem.200700840. URL: https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/chem.200700840
7. Zu L., Zhang S., Xie H., Wang W. Catalytic asymmetric oxa-Michael-Michael cascade for facile construction of chiral chromans via an aminal intermediate // Org. Lett. 2009. Vol. 11, no. 7. P. 1627-1630.
8. Yu H., Xu P., He H., Zhu J., Lin H., Han S. Highly enantioselective Biginelli reactions using methanopyroline/thiourea–based dual organocatalyst systems: asymmetric synthesis of 4-substituted unsaturated aryl dihydropyrimidines // Tetrahedron: Asymmetry. 2017. Vol. 28, no. 2. P. 257-265.
9. Hu N., Li K., Wang Z., Tang W. Synthesis of chiral 1,4-benzodioxanes and chromans by enantioselective palladium-catalyzed alkene aryloxyarylation reactions // Angew. Chem., Int. Ed. 2016. Vol. 55, no. 16. P. 5044 5048.
10. Filimonov S.I., Chirkova Zh.V., Kabanova M.V., Makarova E.S., Shetnev A.A., Panova V.A., Suponitsky K.Yu. A sondensation of Biginelli products with 1,3-benzenediols: a facile access to diastereomerically pure hexahydro-5H-chromeno[4,3-d]pyrimidin-5-ones // ChemistrySelect. 2019. Vol. 4, no. 33. P. 9550-9555. DOI:https://doi.org/10.1002/slct.201901997. URL: https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/slct.201901997
11. Makarova E.S., Kabanova M.V., Filimonov C.I., Shetnev A.A., Suponickiy K.Yu. Sintez i modifikaciya po gidroksil'noy gruppe zameschennyh geksagidro-2H-hromeno[4,3-d]pirimidin-2,5-dionov // Izv. AN. Ser. him. 2022, № 5. S. 1034-1042.
12. Filimonov S.I., Makarova E.S., Chirkova Zh.V., Kabanova M.V. Diastereomernyy sostav reakcii obrazovaniya geksagidro-5N-hromeno[4,3-d]pirimidin-5-onov // Ot himii k tehnologii shag za shagom. 2022. T. 3, № 1. S. 68-75. URL: http://chemintech.ru/index.php/tor/2022tom3no1
