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From Chemistry Towards Technology Step-By-Step
Journals / From Chemistry Towards Technology Step-By-Step / Volume 4 Issue 2 / Diastereoselective synthesis of chromeno[4,3-d]pyrimidines
UDC 547.814.1 UDC 547.853.3

DIASTEREOSELECTIVE SYNTHESIS OF CHROMENO[4,3-D]PYRIMIDINES Diastereoselective synthesis of chromeno[4,3-d]pyrimidines

Published in From Chemistry Towards Technology Step-By-Step · Volume 4, Issue 2 · Pages 17–23 · Rubric: Scientific articles
DOI: https://doi.org/10.52957/2782-1900-2024-4-2-17-23
Received: 28.04.2023 Accepted: 12.05.2023 Published: 23.06.2023
Authors
AN
Anastasia Uryadova
EL
Elena Makarova
SE
Sergey Filimonov
ABSTRACT
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
KEYWORDS
geksagidrohromeno[4, 3-d]pirimidinny, rezorcin, kislotno-kataliziruemaya kondensaciya, diastereonapravlennost'
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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

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