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Orthoamide und Iminiumsalze, CVIII. Umsetzungen von Orthoamiden der Alkincarbonsäuren mit CH/NH-aciden, tautomeriefähigen Verbindungen

  • Willi Kantlehner EMAIL logo , Kai Edelmann , Markus Vettel and Wolfgang Frey
Published/Copyright: February 13, 2023
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Zeitschrift für Naturforschung B
From the journal Zeitschrift für Naturforschung B Volume 78 Issue 5

Abstract

The reaction of keten-O,N-acetals, which can exist in tautomeric forms, with orthoamides of alkine carboxylic acids 4 affords pyridine carboxylic acid esters or -nitriles. Analogous reactions of the orthoamides 4 with imidazole-2-yliden-acetic acid ester or -acetonitrile deliver imidazo[1,2-a]pyridines. From N-alkyl-3,3-diamino-acrylic acid derivatives and orthoamides of propiolic acid 4-aza-heptatriencarbonitriles can be prepared, whereas orthoamides of phenylpropiolic acid deliver directly 2H-pyrimidine-2-ylidene-cyanacetic acid derivatives. 4-Amino-cumarine reacts with orthoamides 4 to give isomeric 5-oxo-[1]-benzopyrano[4,3-b]pyridines. The orthoamides 4 transform 1,3-diimino-isoindolin into 2-cyanphenylpyrimidines. 2-(Pyrazol-1-yl)-benzamides can be prepared from 3-indazolinon and orthoamides 4. The reaction of orthoamides 4 with 6-amino-1,3-dimethyl-uracil proceeds in a complex manner and gives primary products which are very likely imidazo-diazepines. By thermolysis of one of these products a fluorescent pyrolo-imidazolidindione is obtained, which was alkylated with triethyloxonium tetrafluoroborate to give a quaternary ammonium tetrafluoroborate.

Keywords: condensation reactions; keten-O,N-acetals; ketenaminals; orthoamides of alkyne carboxylic acids; pyridines; pyrimidines
Corresponding author: Willi Kantlehner, Abteilung Technische Organische Synthesechemie und Katalyseforschung, Institut für Angewandte Forschung, Hochschule Aalen, Beethovenstr. 1, D-73430 Aalen, Germany; and Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart, Germany, E-mail:
Herrn Prof. Dr. Horst Hartmann zum 85. Geburtstag gewidmet.

Orthoamide und Iminiumsalze CVII, see ref. [1].

  1. Author contribution: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: None declared.

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

References

1. Kantlehner, W., Vettel, M., Lehmann, H., Frey, W. Z. Naturforsch. 2022, 77b, 809–829.10.1515/znb-2022-0051Search in Google Scholar

2. Kantlehner, W., Speh, P., Lehmann, H., Bräuner, H.-J., Haug, E., Mergen, W. W. Chem. Ztg. 1990, 114, 176–178.Search in Google Scholar

3. Kantlehner, W., Vettel, M., Lehmann, H., Edelmann, K., Stieglitz, R., Ivanov, J. C. J. Prakt. Chem. Chem. Ztg. 1998, 340, 401–423.Search in Google Scholar

4. Kantlehner, W., Haug, E., Stieglitz, R., Frey, W., Kreß, R., Mezger, J. Z. Naturforsch. 2002, 57b, 399–419.10.1515/znb-2002-0406Search in Google Scholar

5. Kantlehner, W., Mezger, J., Stieglitz, R., Edelmann, K., Lehmann, H., Vettel, M., Kreß, R., Frey, W., Ladendorf, S. Z. Naturforsch. 2007, 62b, 1015–1029.10.1515/znb-2007-0804Search in Google Scholar

6. Kantlehner, W., Mezger, J., Kreß, R., Frey, W. Z. Naturforsch. 2018, 73b, 437–455.10.1515/znb-2018-0011Search in Google Scholar

7. Kantlehner, W., Edelmann, K., Frey, W. Z. Naturforsch. 2018, 73b, 623–634.10.1515/znb-2018-0064Search in Google Scholar

8. Kantlehner, W., Mezger, J., Lehmann, H., Edelmann, K., Frey, W. Z. Naturforsch. 2018, 73b, 689–702.10.1515/znb-2018-0065Search in Google Scholar

9. Kantlehner, W., Lehmann, H., Stieglitz, R., Frey, W. Z. Naturforsch. 2019, 74b, 913–924.10.1515/znb-2019-0077Search in Google Scholar

10. Kantlehner, W., Stieglitz, R., Lehmann, H., Vettel, M. Z. Naturforsch. 2019, 74b, 925–938.10.1515/znb-2019-0078Search in Google Scholar

11. Kantlehner, W., Edelmann, K., Mezger, J., Vettel, M., Frey, W. Z. Naturforsch. 2021, 76b, 417–430.10.1515/znb-2021-0005Search in Google Scholar

12. Kantlehner, W., Lehmann, H., Edelmann, K., Mezger, J., Frey, W. Z. Naturforsch. 2022, 77b, 565–581.10.1515/znb-2021-0096Search in Google Scholar

13. Kantlehner, W., Edelmann, K., Vettel, M. Z. Naturforsch. 2022, 77b, 743–755.10.1515/znb-2022-0050Search in Google Scholar

14. Haarmann, W., Müller, E., Narr, B., Nickel, J., Roch, J. Thomae GmbH, Patent DE 2643753 1976; Chem. Abstr. 1978, 89, 6322.Search in Google Scholar

15. Meyer, H., Kurz, J. Liebigs Ann. Chem. 1978, 1491–1504; https://doi.org/10.1002/jlac.197819780914.Search in Google Scholar

16. Meyer, H. Liebigs Ann. Chem. 1981, 1523–1533; https://doi.org/10.1002/jlac.198119810902.Search in Google Scholar

17. Jones, R. C. F., Hirst, S. C. Tetrahedron Lett. 1989, 30, 5361–5364; https://doi.org/10.1016/s0040-4039(01)93787-6.Search in Google Scholar

18. Jones, R. C. F., Smallridge, M. J. Tetrahedron Lett. 1988, 29, 5005–5008; https://doi.org/10.1016/s0040-4039(00)80665-6.Search in Google Scholar

19. Huang, Z., Lin, Z., Liu, Z. Heterocycles 1986, 24, 2247–2254; https://doi.org/10.3987/r-1986-08-2247.Search in Google Scholar

20. Huang, Z., Lin, Z. Synth. Commun. 1989, 19, 1801–1812; https://doi.org/10.1080/00397918908051079.Search in Google Scholar

21. Coenen, M., Faust, J., Ringel, C., Mayer, R. J. Prakt. Chem. 1965, 27, 239–250; https://doi.org/10.1002/prac.19650270503.Search in Google Scholar

22. Kantlehner, W., Vettel, M., Lehmann, H., Edelmann, K., Stieglitz, R., Ivanov, I. C. J. Prakt. Chem. 1998, 340, 408–423; https://doi.org/10.1002/prac.19983400503.Search in Google Scholar

23. Kantlehner, W., Stieglitz, R., Hauber, M., Haug, E., Regele, C. J. Prakt. Chem. 2000, 343, 256–268; https://doi.org/10.1002/(sici)1521-3897(200003)342:3<256::aid-prac256>3.0.co;2-g.10.1002/(SICI)1521-3897(200003)342:3<256::AID-PRAC256>3.0.CO;2-GSearch in Google Scholar
Erhalten: 2022-08-08
Angenommen: 2022-09-26
Online erschienen: 2023-02-13
Erschienen im Druck: 2023-05-25

© 2023 Walter de Gruyter GmbH, Berlin/Boston

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https://doi.org/10.1515/znb-2022-0113
Keywords for this article
condensation reactions; keten-O,N-acetals; ketenaminals; orthoamides of alkyne carboxylic acids; pyridines; pyrimidines

Articles in the same Issue

  1. Frontmatter
  2. In this issue
  3. Research Articles
  4. Photoredox-catalyzed three-component difluorobenzylation of quinoxalin-2(1H)-ones with unactivated vinylarenes and BrCF2CO2Et/HCF2CO2H
  5. Catalyst-free direct synthesis of indeno[1,2-b]indol-5(4bH)-yl benzimidamides
  6. Crystal structure of three chloridocuprate(I, II) complexes with methylene blue (MB) counterions
  7. Crystal structure, photophysical properties, and DFT calculations of a boron difluoride curcumin complex
  8. The double cluster compound [Nb6Cl14(MeCN)4][Nb6Cl14(pyz)4]·6MeCN (Me: methyl, pyz: pyrazine) with a layered structure resulting from weak intermolecular interactions
  9. Expanding transition metal borate chemistry to include main group elements: high-pressure synthesis and structural relation of β-MgB4O7
  10. Eu2Ru3Si5 and Eu2Ir3Ga5 – first europium compounds with U2Mn3Si5-type structure but different europium valence
  11. Mössbauer-spectroscopic characterization of the stannides Sr2Pd2Sn and Eu2Pd2Sn
  12. Orthoamide und Iminiumsalze, CVIII. Umsetzungen von Orthoamiden der Alkincarbonsäuren mit CH/NH-aciden, tautomeriefähigen Verbindungen
  13. Book Review
  14. Thomas J. Meade (Guest Editor), Astrid Sigel, Helmut Sigel, Eva Freisinger, Roland K. O. Sigel (Series Editors): Molecular Bio-Sensors and the Role of Metal Ions
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