Unexpected cascade transformations in the reaction of aromatic aldehydes with the malononitrile dimer

References

• Tverdokhleb, N. M.; Khoroshilov, G. E.; Dotsenko, V. V. Cascade Synthesis of Pyrido[3,2-A]Indolizines by Reaction of Kröhnke–Mukaiyama Salts with Malononitrile Dimer. Tetrahedron Lett. 2014, 55, 6593–6595. DOI: 10.1016/j.tetlet.2014.10.046.
   Web of Science ®Google Scholar
• Yoon, C.; Choi, J. Synthesis of Tricyanopyrrolidone Derivatives as Synergists for Improving Contrast Ratio of Liquid Crystal Displays. Dyes Pigm. 2014, 101, 344–350. DOI: 10.1016/j.dyepig.2013.10.017.
   Web of Science ®Google Scholar
• Bürckstümmer, H.; Kronenberg, N. M.; Meerholz, K.; Würthner, F.; Near-Infrared Absorbing Merocyanine Dyes for Bulk Heterojunction Solar Cells. Org. Lett. 2010, 12, 3666–3669. DOI: 10.1021/ol101492q.
   PubMed Web of Science ®Google Scholar
• Ibrahim, M. A.; El-Gohary, N. M. Studies on the Chemical Transformations of 6-Methylchromone-3-Carbonitrile under Nucleophilic Conditions. J. Heterocyclic Chem. 2016, 53, 859–864. DOI: 10.1002/jhet.2355.
   Web of Science ®Google Scholar
• Belikov, M. Y.; Fedoseev, S. V.; Ershov, O. V.; Ievlev, M. Y.; Tafeenko, V. A. Rearrangement of 4-Oxobutane-1,1,2,2-Tetracarbonitriles to the Penta-1,3-Diene-1,1,3-Tricarbonitrile Moiety as an Approach to Novel Acceptors for Donor–Acceptor Chromophores. Tetrahedron Lett. 2016, 57, 4101–4104. DOI: 10.1016/j.tetlet.2016.07.095.
   Web of Science ®Google Scholar
• Belikov, M. Y.; Ievlev, M. Y.; Milovidova, A. G.; Ershov, O. V. Synthesis of 2-(5-Aryl-4-Methyl-2-Oxo-1,2-Dihydro-3H-Pyrrol-3-Ylidene)Malononitriles. Russ. J. Org. Chem. 2017, 53, 1601–1603. DOI: 10.1134/S1070428017100207.
   Web of Science ®Google Scholar
• Fedoseev, S. V.; Belikov, M. Y.; Ershov, O. V.; Bardasov, I. N.; Tafeenko, V. A. New Push–Pull Chromophores. Synthesis of 2-[4-Aryl-3-Cyano-5-Hydroxy-5-Methyl-1H-Pyrrol-2(5H)-Ylidene]Malononitriles. Russ. J. Org. Chem. 2016, 52, 1440–1443. DOI: 10.1134/S1070428016100122.
   Web of Science ®Google Scholar
• Moustafa, M.; Al-Mousawi, S.; Hilmy, N.; Ibrahim, Y.; Liermann, J.; Meier, H.; Elnagdi, M. Unexpected Behavior of Enaminones: Interesting New Routes to 1,6-Naphthyridines, 2-Oxopyrrolidines and Pyrano[4,3,2-de][1,6]Naphthyridines. Molecules. 2012, 18, 276–286. DOI: 10.3390/molecules18010276.
   PubMed Web of Science ®Google Scholar
• Khodairy, A. Synthesis of Pyrazolo[3,4-B]- and Pyrido[2,3-B]-1,5-Benzodiazepines. Synth. Commun. 2011, 41, 612–621. DOI: 10.1080/00397911003629507.
   Web of Science ®Google Scholar
• Dotsenko, V. V.; Ismiev, A. I.; Khrustaleva, A. N.; Frolov, K. A.; Krivokolysko, S. G.; Chigorina, E. A.; Snizhko, A. P.; Gromenko, V. M.; Bushmarinov, I. S.; Askerov, R. K.; et al. Synthesis, Structure, and Reactions of (4-Aryl-3-Cyano-6-Oxopiperidin-2-Ylidene)Malononitriles. Chem. Heterocycl. Comp. 2016, 52, 473–483. DOI: 10.1007/s10593-016-1918-3.
   Web of Science ®Google Scholar
• Dotsenko, V. V.; Chigorina, E. A.; Krivokolysko, S. G. Synthesis of Derivatives of a Novel Heterocyclic System 7-Thia-1,4,6,8-Tetraazabenzo[de]Anthracene. Chem. Heterocycl. Comp. 2017, 53, 626–628. DOI: 10.1007/s10593-017-2103-z.
   Web of Science ®Google Scholar
• Bardasov, I. N.; Alekseeva, A. U.; Yaschenko, N. N.; Zhitar, S. V.; Lyshchikov, A. N. One-Pot Synthesis of Annulated 1,8-Naphthyridines. Heterocycl. Commun. 2017, 23, 269–273. DOI: 10.1515/hc-2017-0068.
   Web of Science ®Google Scholar
• Li, J.; Yu, Y.; Tu, M.-S.; Jiang, B.; Wang, S.-L.; Tu, S.-J. New Domino Heteroannulation of Enaminones: Synthesis of Diverse Fused Naphthyridines. Org. Biomol. Chem. 2012, 10, 5361. DOI: 10.1039/c2ob25349f.
   PubMed Web of Science ®Google Scholar
• Alekseeva, A. Y.; Mikhailov, D. L.; Bardasov, I. N.; Timrukova, D. V.; Ershov, O. V. Three-Component Synthesis of 5-Aryl-1,8-Naphthyridine-3-Carbonitriles. Russ. J. Org. Chem. 2016, 52, 1463–1467. DOI: 10.1134/S1070428016100158.
   Web of Science ®Google Scholar
• Alekseeva, A. Y.; Bardasov, I. N.; Mikhailov, D. L.; Ershov, O. V. Synthesis of Fused Derivatives of 1,8-Naphthyridine. Russ. J. Org. Chem. 2017, 53, 1243–1248. DOI: 10.1134/S1070428017080140.
   Web of Science ®Google Scholar
• Shao, X.; Li, Z.; Sun, F.; Zhu, F. One-Pot, Three-Component Synthesis of 1,8-Naphthyridine Derivatives from Heterocyclic Ketene Aminals, Malononitrile Dimer, and Aryl Aldehydes. Synlett 2015, 26, 2306–2312. DOI: 10.1055/s-0034-1378823.
   Web of Science ®Google Scholar
• Shaabani, A.; Hooshmand, S. E.; Tabatabaei, A. T. Synthesis of Fully Substituted Naphthyridines: A Novel Domino Four-Component Reaction in a Deep Eutectic Solvent System Based on Choline Chloride/Urea. Tetrahedron Lett. 2016, 57, 351–353. DOI: 10.1016/j.tetlet.2015.12.017.
   Google Scholar
• Alekseeva, A. Y.; Mikhailov, D. L.; Bardasov, I. N.; Ershov, O. V.; Nasakin, O. E. One-Stage Synthesis of Highly Functionalized N-Substituted 1,8-Naphthyridines. Russ. J. Org. Chem. 2013, 49, 1715–1717. DOI: 10.1134/S1070428013110286.
   Web of Science ®Google Scholar
• Abdelmoniem, A. M.; Ghozlan, S. A. S.; Abdelmoniem, D. M.; Elwahy, A. H. M.; Abdelhamid, I. A. Facile One-Pot, Three-Component Synthesis of Novel Bis-Heterocycles Incorporating 5H-Chromeno[2,3-B] Pyridine-3-Carbonitrile Derivatives. J. Heterocyclic Chem. 2017, 54, 2844–2849. DOI: 10.1002/jhet.2890.
   Web of Science ®Google Scholar
• Bardasov, I. N.; Alekseeva, A. Y.; Malyshkina, N. L.; Ershov, O. V.; Grishanov, D. A. One-Step Synthesis of Chromeno[2,3-B]Pyridines. Russ. J. Org. Chem. 2016, 52, 830–833. DOI: 10.1134/S1070428016060117.
   Web of Science ®Google Scholar
• Melekhin, E. A.; Bardasov, I. N.; Ershov, O. V.; Eremkin, A. V.; Kayukov, Y. S.; Nasakin, O. E. Synthesis of 5-Aryl-2,4-Diamino-8-Hydroxy-5H-Chromeno[2,3-B]Pyridine-3-Carbonitriles. Russ. J. Org. Chem. 2006, 42, 622–623. DOI: 10.1134/S1070428006040269.
   Web of Science ®Google Scholar
• Bardasov, I. N.; Alekseeva, A. U.; Mihailov, D. L.; Ershov, O. V.; Grishanov, D. A. Double Heteroannulation Reactions of 1-Naphthol with Alkyl- and Arylmethylidene Derivatives of Malononitrile Dimer. Tetrahedron Lett. 2015, 56, 1830–1832. DOI: 10.1016/j.tetlet.2015.02.081.
   Web of Science ®Google Scholar
• Tu, X.-J.; Fan, W.; Hao, W.-J.; Jiang, B.; Tu, S.-J. Three-Component Bicyclization Providing an Expedient Access to Pyrano[2′,3′:5,6]Pyrano[2,3-B]Pyridines and Its Derivatives. ACS Comb. Sci. 2014, 16, 647–651. DOI: 10.1021/co500100c.
   PubMed Web of Science ®Google Scholar
• Bardasov, I. N.; Alekseeva, A. U.; Ershov, O. V.; Belikov, M. Y. Four Component DHARMA-Synthesis of Some Densely Functionalized 1,8-Naphthyridines. Tetrahedron Lett. 2015, 56, 5434–5436. DOI: 10.1016/j.tetlet.2015.08.013.
   Web of Science ®Google Scholar
• Crystallographic data (excluding structure factors) for the structure 4b in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 1907750. Copies of the data can be obtained free of charge from The Cambridge Crystallographic Data Centre via http://www.ccdc.cam.ac.uk/data_request/cif.
   Google Scholar
• Bardasov, I. N.; Alekseeva, A. U.; Chunikhin, S. S.; Shishlikova, M. A.; Ershov, O. V. Synthesis and Characterization of 2-(4-Aryl-3-Cyano-6-Methylpyridin-2(1H)-Ylidene)Malononitriles. Tetrahedron Lett. 2019, 60, 1170–1173. DOI: 10.1016/j.tetlet.2019.03.054.
   Web of Science ®Google Scholar
• Bardasov, I. N.; Alekseeva, A. U.; Mihailov, D. L.; Ershov, O. V.; Nasakin, O. E.; Tafeenko, V. A. One-Pot Synthesis of 2-(Dicyanomethylene)-1,2-Dihydropyridine Derivatives. Tetrahedron Lett. 2014, 55, 2730–2733. DOI: 10.1016/j.tetlet.2014.03.056.
   Web of Science ®Google Scholar
• Chunikhin, S. S.; Ershov, O. V.; Ievlev, M. Y.; Belikov, M. Y.; Tafeenko, V. A. Novel Chromophores of Cyanopyridine Series with Strong Solvatochromism and near-Infrared Solid-State Fluorescence. Dyes Pigm. 2018, 156, 357–368. DOI: 10.1016/j.dyepig.2018.04.024.
   Web of Science ®Google Scholar
• Ershov, O. V.; Bardasov, I. N. Synthesis of Pyridine Derivatives Containing a Tricyanobutadiene Motif (Microreview). Chem. Heterocycl. Comp. 2017, 53, 1178–1180. DOI: 10.1007/s10593-018-2190-5.
   Web of Science ®Google Scholar
• Bardasov, I. N.; Alekseeva, A. U.; Chunikhin, S. S.; Ershov, O. V. Three-Component Synthesis and Characterization of Nicotinamide Derivatives Containing a Buta-1,3-Diene-1,1,3-Tricarbonitrile Fragment. Synth. Commun. 2018, 48, 2600–2607. DOI: 10.1080/00397911.2018.1515959.
   Web of Science ®Google Scholar
• Bardasov, I. N.; Alekseeva, A. Y.; Chunikhin, S. S.; Ershov, O. V. Three-Component Synthesis and Optical Properties of Nicotinic Acid Esters Containing Buta-1,3-Dien-1,1,3-Tricarbonitrile Fragment. Russ. J. Org. Chem. 2018, 54, 1161–1165. DOI: 10.1134/S1070428018080079.
   Web of Science ®Google Scholar
• Sheldrick, G. M. A Short History of SHELX. Acta Crystallogr. 2008, 64, 112–122. DOI: 10.1107/s0108767307043930.
   PubMed Web of Science ®Google Scholar