Thermal Rearrangement of 5-(2-Hydroxy-6-oxocyclohexyl)-5-chromeno[2,3-]pyridines

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2023 Apr 13

PMID 37049908

Authors

Yuliya E Ryzhkova

Fedor V Ryzhkov

Michail N Elinson

Anatoly N Vereshchagin

Roman A Novikov

Artem N Fakhrutdinov

Affiliations

Soon will be listed here.

Abstract

Some of the most important transformations in organic chemistry are rearrangement reactions, which play a crucial role in increasing synthetic efficiency and molecular complexity. The development of synthetic strategies involving rearrangement reactions, which can accomplish synthetic goals in a very efficient manner, has been an evergreen topic in the synthetic chemistry community. Xanthenes, pyridin-2(1)-ones, and 1,6-naphthyridines have a wide range of biological activities. In this work, we propose the thermal rearrangement of 7,9-dihalogen-substituted 5-(2-hydroxy-6-oxocyclohexyl)-5-chromeno[2,3-]pyridines in DMSO. Previously unknown 5,7-dihalogenated 5-(2,3,4,9-tetrahydro-1-xanthen-9-yl)-6-oxo-1,6-dihydropyridines and 10-(3,5-dihalogen-2-hydroxyphenyl)-5,6,7,8,9,10-hexahydrobenzo[][1,6]naphthyridines were synthesized with excellent yields (90-99%). The investigation of the transformation using H-NMR monitoring made it possible to confirm the ANRORC mechanism. The structures of synthesized compounds were confirmed by 2D-NMR spectroscopy.

References

Wu X, Ma Z, Feng T, Zhu C . Radical-mediated rearrangements: past, present, and future. Chem Soc Rev. 2021; 50(20):11577-11613. DOI: 10.1039/d1cs00529d. View

Kumar A, Sharma S, Maurya R, Sarkar J . Diversity oriented synthesis of benzoxanthene and benzochromene libraries via one-pot, three-component reactions and their anti-proliferative activity. J Comb Chem. 2009; 12(1):20-4. DOI: 10.1021/cc900143h. View

Austin N, Hadley M, Harling J, Harrington F, Macdonald G, Mitchell D . The design of 8,8-dimethyl[1,6]naphthyridines as potential anticonvulsant agents. Bioorg Med Chem Lett. 2003; 13(10):1627-9. DOI: 10.1016/s0960-894x(03)00288-9. View

Shams H, Mohareb R, Helal M, Mahmoud A . Novel synthesis and antitumor evaluation of polyfunctionally substituted heterocyclic compounds derived from 2-cyano-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-acetamide. Molecules. 2010; 16(1):52-73. PMC: 6259152. DOI: 10.3390/molecules16010052. View

Maharvi G, Ali S, Riaz N, Afza N, Malik A, Ashraf M . Mild and efficient synthesis of new tetraketones as lipoxygenase inhibitors and antioxidants. J Enzyme Inhib Med Chem. 2008; 23(1):62-9. DOI: 10.1080/14756360701408754. View

Sato N, Jitsuoka M, Shibata T, Hirohashi T, Nonoshita K, Moriya M . (9S)-9-(2-hydroxy-4,4-dimethyl-6-oxo-1-cyclohexen-1-yl)-3,3-dimethyl-2,3,4,9-tetrahydro-1H-xanthen-1-one, a selective and orally active neuropeptide Y Y5 receptor antagonist. J Med Chem. 2008; 51(15):4765-70. DOI: 10.1021/jm8003587. View

Salvador J, Pinto R, Santos R, Le Roux C, Matos Beja A, Paixao J . Bismuth triflate-catalyzed Wagner-Meerwein rearrangement in terpenes. Application to the synthesis of the 18alpha-oleanane core and A-neo-18alpha-oleanene compounds from lupanes. Org Biomol Chem. 2009; 7(3):508-17. DOI: 10.1039/b814448f. View

Barakat A, Al-Majid A, Al-Qahtany B, Ali M, Teleb M, Al-Agamy M . Synthesis, antimicrobial activity, pharmacophore modeling and molecular docking studies of new pyrazole-dimedone hybrid architectures. Chem Cent J. 2018; 12(1):29. PMC: 5852137. DOI: 10.1186/s13065-018-0399-0. View

Ghoneim A, El-Farargy A, Abdelaziz S . Synthesis and antimicrobial activities of new s-nucleosides of chromeno[2,3-B]pyridine derivatives and C-nucleosides of [1,2,4]triazolo[1,5-a]quinoline derivatives. Nucleosides Nucleotides Nucleic Acids. 2014; 33(9):583-96. DOI: 10.1080/15257770.2014.912320. View

10.

Palumbo Piccionello A, Guarcello A, Buscemi S, Vivona N, Pace A . Synthesis of amino-1,2,4-triazoles by reductive ANRORC rearrangements of 1,2,4-oxadiazoles. J Org Chem. 2010; 75(24):8724-7. DOI: 10.1021/jo102049r. View

11.

Weatherhead G, Cortez G, Schrock R, Hoveyda A . Mo-catalyzed asymmetric olefin metathesis in target-oriented synthesis: enantioselective synthesis of (+)-africanol. Proc Natl Acad Sci U S A. 2004; 101(16):5805-9. PMC: 395989. DOI: 10.1073/pnas.0307589101. View

12.

Ruchelman A, Singh S, Ray A, Wu X, Yang J, Li T . 5H-Dibenzo[c,h]1,6-naphthyridin-6-ones: novel topoisomerase I-targeting anticancer agents with potent cytotoxic activity. Bioorg Med Chem. 2003; 11(9):2061-73. DOI: 10.1016/s0968-0896(03)00051-8. View

13.

Mohareb R, Abouzied A, Abbas N . Synthesis and Biological Evaluation of Novel 4,5,6,7-Tetrahydrobenzo[D]-Thiazol-2- Yl Derivatives Derived from Dimedone with Anti-Tumor, C-Met, Tyrosine Kinase and Pim-1 Inhibitions. Anticancer Agents Med Chem. 2019; 19(12):1438-1453. DOI: 10.2174/1871520619666190416102144. View

14.

Romanov-Michailidis F, Guenee L, Alexakis A . Enantioselective organocatalytic fluorination-induced Wagner-Meerwein rearrangement. Angew Chem Int Ed Engl. 2013; 52(35):9266-70. DOI: 10.1002/anie.201303527. View

15.

Wolf J, Stuer W, Grunwald C, Werner H, Schwab P, Schulz M . Ruthenium Trichloride, Tricyclohexyl- phosphane, 1-Alkynes, Magnesium, Hydrogen, and Water-Ingredients of an Efficient One-Pot Synthesis of Ruthenium Catalysts for Olefin Metathesis. Angew Chem Int Ed Engl. 2018; 37(8):1124-1126. DOI: 10.1002/(SICI)1521-3773(19980504)37:8<1124::AID-ANIE1124>3.0.CO;2-C. View

16.

Ahmed Mekheimer R, Sayed A, Ahmed E . Novel 1,2,4-triazolo[1,5-a]pyridines and their fused ring systems attenuate oxidative stress and prolong lifespan of Caenorhabiditis elegans. J Med Chem. 2012; 55(9):4169-77. DOI: 10.1021/jm2014315. View

17.

Ryzhkova Y, Ryzhkov F, Fakhrutdinov A, Elinson M . Oxidative Cyclization of 5-Chromeno[2,3-]pyridines to Benzo[]chromeno[4,3,2-][1,6]naphthyridines, Their NMR Study and Computer Evaluation as Material for LED. Molecules. 2022; 27(13). PMC: 9268656. DOI: 10.3390/molecules27134156. View

18.

Gallardo-Fuentes S, Contreras R . Mechanistic insights into the ANRORC-like rearrangement between methylhydrazine and 1,2,4-oxadiazole derivatives. Org Biomol Chem. 2015; 13(36):9439-44. DOI: 10.1039/c5ob01300c. View

19.

Zhang X, Li B, Wang S, Zhang K, Zhang F, Tu Y . Recent development and applications of semipinacol rearrangement reactions. Chem Sci. 2021; 12(27):9262-9274. PMC: 8314203. DOI: 10.1039/d1sc02386a. View

20.

Galatsis P, Yamagata K, Wendt J, Connolly C, Mickelson J, Milbank J . Synthesis and SAR comparison of regioisomeric aryl naphthyridines as potent mGlu5 receptor antagonists. Bioorg Med Chem Lett. 2007; 17(23):6525-8. DOI: 10.1016/j.bmcl.2007.09.083. View