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Orthoamide und Iminiumsalze, CV. Umsetzungen von Orthoamiden der Alkincarbonsäuren mit Carbonsäureamiden

  • Willi Kantlehner EMAIL logo , Hansjörg Lehmann , Kai Edelmann , Jochen Mezger and Wolfgang Frey
Published/Copyright: July 4, 2022
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Zeitschrift für Naturforschung B
From the journal Zeitschrift für Naturforschung B Volume 77 Issue 7-8

Abstract

The reaction of an orthoamide derivative of phenylpropiolic acid (22a) with primary and secondary amides gives rise to the formation of a wide spectrum of reaction products. The reaction of 22a with formamide delivers a N-carbamoyl-cinnamic acid amidine, wheras the analogous reaction with methylene-diformamide leads to a ketenaminal, which is substituted in β-position by a N-formylimino group. From the orthoamide 22a and phthalimide a phthalic acid amide amidine is obtained. In contrast the reaction of diformamide with 22a affords a β-imino enamine. 2,6-Diaminopyridines can be obtained from 22a with acetamide, propionamide and butyramide in low yields. The pyridines are characterized as perchlorates. From 22a and benzamide a 4-amino-2,6-diphenylpyrimidine is obtained in low yield. In the reaction of the closely related orthoamide derivative of 4-Cl-phenylpropiolic acid 22b with benzamide are isolated as a further products two pyrimidine derivatives. A pyrimidinone and a vinylogous thiourea can be obtained from 22a and urea and thiourea, respectively.

Keywords: carboxylic acid amides; condensation reaction; N-functionalized amidines; orthoamides of alkyne carboxylic acids; pyridines; pyrimidines
Corresponding author: Willi Kantlehner, Institut für Angewandte Forschung, Abteilung Technische Organische Synthesechemie und Katalyseforschung, Hochschule Aalen, Beethovenstr. 1, D-73430 Aalen, Germany; und Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart, Germany, E-mail:

Orthoamide und Iminiumsalze CIV, 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.

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Erhalten: 2021-07-09
Angenommen: 2022-05-05
Online erschienen: 2022-07-04
Erschienen im Druck: 2022-07-26

© 2022 Walter de Gruyter GmbH, Berlin/Boston

Articles in the same Issue

  1. Frontmatter
  2. In this issue
  3. Research Articles
  4. Electron density of a benzoylated tetrafructopyranose
  5. Die Reihe der nicht-zentrosymmetrischen tetragonalen Lanthanoid(III)-Oxidoantimonat(III)-Chloride LnSb2O4Cl (Ln = Gd–Lu)
  6. Iminium-substituted 2,3-dihydroisoxazoles: synthesis from acetylenic iminium salts and nitrones, and some transformations
  7. Reactions of 1-trifluoromethyl-prop-2-yne1-iminium salts with 2- and 3-aminopyridines
  8. 2,5-Dihydroxy-1,4-quinones appended with two phosphinyl groups: syntheses, structures, and redox properties
  9. Ordered CaCu5-type phases REPd2Zn3 (RE = Y, La–Nd, Sm, Gd–Dy)
  10. The solid solutions TbCuIn1–x M x (M = Al, Ga)
  11. Synthesis and structural characterization of a luminescent cadmium(II) complex with bis(4-(1H-imidazole-1-yl)phenyl)amine and 4,4′-sulfonyldibenzoate ligands
  12. Synthesis and structure of a zinc(II) coordination polymer assembled with 5-(3-carboxybenzyloxy)isophthalic acid and 1,2-bis(4-pyridyl)ethane
  13. Orthoamide und Iminiumsalze, CV. Umsetzungen von Orthoamiden der Alkincarbonsäuren mit Carbonsäureamiden
  14. Notes
  15. Addendum to: bixbyite-type phases in the system Ta-Zr-O-N
  16. Addendum to: Crystal structure of mechanochemically synthesized Ag2CdSnS4
  17. Addendum to: FeBiS2Cl – a new iron-containing member of the MPnQ 2 X family
https://doi.org/10.1515/znb-2021-0096
Keywords for this article
carboxylic acid amides; condensation reaction; N-functionalized amidines; orthoamides of alkyne carboxylic acids; pyridines; pyrimidines

Articles in the same Issue

  1. Frontmatter
  2. In this issue
  3. Research Articles
  4. Electron density of a benzoylated tetrafructopyranose
  5. Die Reihe der nicht-zentrosymmetrischen tetragonalen Lanthanoid(III)-Oxidoantimonat(III)-Chloride LnSb2O4Cl (Ln = Gd–Lu)
  6. Iminium-substituted 2,3-dihydroisoxazoles: synthesis from acetylenic iminium salts and nitrones, and some transformations
  7. Reactions of 1-trifluoromethyl-prop-2-yne1-iminium salts with 2- and 3-aminopyridines
  8. 2,5-Dihydroxy-1,4-quinones appended with two phosphinyl groups: syntheses, structures, and redox properties
  9. Ordered CaCu5-type phases REPd2Zn3 (RE = Y, La–Nd, Sm, Gd–Dy)
  10. The solid solutions TbCuIn1–x M x (M = Al, Ga)
  11. Synthesis and structural characterization of a luminescent cadmium(II) complex with bis(4-(1H-imidazole-1-yl)phenyl)amine and 4,4′-sulfonyldibenzoate ligands
  12. Synthesis and structure of a zinc(II) coordination polymer assembled with 5-(3-carboxybenzyloxy)isophthalic acid and 1,2-bis(4-pyridyl)ethane
  13. Orthoamide und Iminiumsalze, CV. Umsetzungen von Orthoamiden der Alkincarbonsäuren mit Carbonsäureamiden
  14. Notes
  15. Addendum to: bixbyite-type phases in the system Ta-Zr-O-N
  16. Addendum to: Crystal structure of mechanochemically synthesized Ag2CdSnS4
  17. Addendum to: FeBiS2Cl – a new iron-containing member of the MPnQ 2 X family
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