Home Orthoamide und Iminiumsalze, XCIVa. Kondensationsreaktion von Orthoamiden von Alkincarbonsäuren mit 2-Methyl-5-phenacyl-1,3,4-thiadiazolen
Article
Licensed
Unlicensed Requires Authentication

Orthoamide und Iminiumsalze, XCIVa. Kondensationsreaktion von Orthoamiden von Alkincarbonsäuren mit 2-Methyl-5-phenacyl-1,3,4-thiadiazolen

  • Willi Kantlehner EMAIL logo , Kai Edelmann and Wolfgang Frey
Published/Copyright: August 22, 2018
Become an author with De Gruyter Brill
Author Information Explore this Subject
Zeitschrift für Naturforschung B
From the journal Zeitschrift für Naturforschung B Volume 73 Issue 9

Abstract

The ketene aminals 9a–e can be prepared from the orthoamide of propiolic acid 6a and 2-methyl-5-phenacyl-1,3,4-thiadiazoles 8a–e under mild conditions. The crystal structure analyses of 9b and 9d reveal that compounds 9 can be regarded as 1,4-dipoles (push-pull-substituted butadienes). Surprisingly, the analogous reactions of the orthoamides 6b,c with the thiadiazoles 8a–c give rise to the formation of 1,2-dihydro-pyridin-2-thiones 13a–j. The constitution of the compounds 13 was confirmed by crystal structure analyses of the compounds 13c,f,g,i.

Keywords: 1,2-dihydropyridine-2-thiones; 2-phenacyl-1,3,4-thiadiazoles; condensation reactions; orthoamides of alkyne carboxylic acids; push-pull-substituted butadienes

aOrthoamide und Iminiumsalz, XCIII siehe Lit. [1].

Literatur

[1] Orthoamide und Iminiumsalze, XCIII: M. Vettel, H.-J. Bräuner, W. Kantlehner, Z. Naturforsch.2018, 73b, 457.10.1515/znb-2018-0022Search in Google Scholar

[2] R. Stollé, Ber. Dtsch. Chem. Ges. 1899, 32, 797.10.1002/cber.189903201122Search in Google Scholar

[3] R. Stollé, J. Prakt. Chem.1904, 69, 145.10.1002/prac.19040690109Search in Google Scholar

[4] R. Stollé, H. Hille, J. Prakt. Chem.1904, 69, 481.10.1002/prac.19040690133Search in Google Scholar

[5] R. Stollé, G. Zinser, J. Prakt. Chem.1904, 69, 486.10.1002/prac.19040690134Search in Google Scholar

[6] R. Stollé, L. Gutmann, J. Prakt. Chem.1904, 69, 497.10.1002/prac.19040690135Search in Google Scholar

[7] R. Stollé, Ch. Schätzlein, J. Prakt. Chem.1904, 69, 503.10.1002/prac.19040690136Search in Google Scholar

[8] R. Stollé, F. Dellschaft, J. Prakt. Chem.1904, 69, 506.10.1002/prac.19040690137Search in Google Scholar

[9] R. Stollé, J. Prakt. Chem.1904, 70, 424.10.1002/prac.19040700113Search in Google Scholar

[10] R. Stollé, J. Prakt. Chem.1904, 69, 366.10.1002/prac.19040690126Search in Google Scholar

[11] R. Stollé, H. Foerster, J. Prakt. Chem.1904, 69, 382.10.1002/prac.19040690127Search in Google Scholar

[12] R. Stollé, A. Johanaisien, J. Prakt. Chem.1904, 69, 474.10.1002/prac.19040690132Search in Google Scholar

[13] J. Goerdeler, Chem. Ber. 1956, 89, 1534.10.1002/cber.19560890624Search in Google Scholar

[14] H. Hagen, R.-D. Kohler, H. Fleig, Liebigs Ann. Chem.1980, 1216.10.1002/jlac.198019800806Search in Google Scholar

[15] K. J. Reubke in Methoden der Organischen Chemie (Houben-Weyl-Müller), 4. Auflage, Erweiterungs- und Folgebände, Vol. E8, Hetarene III/4 (Ed. E. Schaumann) Thieme Stuttgart, 1994, S. 189.Search in Google Scholar

[16] Bayer AG, DE 2811258, (Erf. H. Fürstenwerth), 1979; Chem. Abstr. 1980, 92, 60311.Search in Google Scholar

[17] Bayer AG, EP 45402, (Erf. H. Fürstenwerth), 1982; Chem. Abstr. 1982, 96, 219268j.Search in Google Scholar

[18] W. Kantlehner, E. Haug, W. Kinzy, H. Hagen, P. Speh, H.-J. Bräuner, Chemiker Ztg.1989, 113, 217.Search in Google Scholar

[19] W. Kantlehner, H. Haug, W. Kinzy, O. Scherr, I. C. Ivanov, Z. Naturforsch.2004, 59b, 366.10.1515/znb-2004-0403Search in Google Scholar

[20] W. Kantlehner, H.-J. Lehmann, K. Edelmann, J. Mezger, I. C. Ivanov, Appl. Catal., A2008, 336, 148.10.1016/j.apcata.2007.08.027Search in Google Scholar

[21] W. Kantlehner, E. Haug, H. Hagen, Liebigs Ann. Chem. 1982, 298.10.1002/jlac.198219820213Search in Google Scholar

[22] W. Kantlehner, G. Simchen, J. Mezger, E. V. Stoyanov, R. Kreß, W. Frey, B. Sievers, Z. Naturforsch. 2005, 60b, 231.10.1515/znb-2005-0218Search in Google Scholar

[23] W. Kantlehner, E. Haug, P. Speh, H.-J. Bräuner, unveröffentlichte Versuche.Search in Google Scholar

[24] W. Kantlehner, M. Vettel, H. Lehmann, K. Edelmann, R. Stieglitz, J. Ivanov, J. Prak. Chem./Chem.-Ztg. 1998, 340, 408.10.1002/prac.19983400503Search in Google Scholar

[25] W. Kantlehner, E. Haug, R. Stieglitz, W. Frey, R. Kreß, J. Mezger, Z. Naturforsch. 2002, 57b, 399.10.1515/znb-2002-0406Search in Google Scholar

[26] W. Kantlehner, J. Mezger, R. Kreß, W. Frey, Z. Naturforsch. 2018, 73b, 437.10.1515/znb-2018-0011Search in Google Scholar

[27] Zh. Krasnaya, T. Stytsenko, V. Bogdanov, A. Dwornikov, Chem. Heterocycl. Comp.1988, 24, 1095.10.1007/BF00475681Search in Google Scholar

[28] W. Kantlehner, R. Kreß, J. Mezger, S. Ladendorf, Z. Naturforsch. 2004, 60b, 227.10.1515/znb-2005-0217Search in Google Scholar

[29] B. Tinant, J.-P. Declercq, D. Bonvy, Z. Janousek, H. G. Viehe, J. Chem. Soc. Perkin Trans. 2, 1993, 911.10.1039/p29930000911Search in Google Scholar

[30] W. Kantlehner, P. Speh, H. Lehmann, H.-J. Bräuner, E. Haug, W. W. Mergen, Chem.-Ztg.1990, 114, 176.Search in Google Scholar

Received: 2018-03-19
Accepted: 2018-06-27
Published Online: 2018-08-22
Published in Print: 2018-09-25

©2018 Walter de Gruyter GmbH, Berlin/Boston

Articles in the same Issue

  1. Frontmatter
  2. In this Issue
  3. NQR, NMR, and X-ray crystal structure studies of [4-C2H5-C6H4NH3]2MBr4 (M=Zn, Cd)
  4. Ein ökonomisches Verfahren zur Aufarbeitung von Reaktionsgemischen bei Lewis-Säure-induzierten elektrophilen Aromatensubstitutionen
  5. Orthoamide und Iminiumsalze, XCIVa. Kondensationsreaktion von Orthoamiden von Alkincarbonsäuren mit 2-Methyl-5-phenacyl-1,3,4-thiadiazolen
  6. Highly effectual synthesis of 4,6-diarylpyrimidin-2(1H)-ones using N,N,N′,N′-tetramethylethylenediaminium-N,N′-disulfonic acid hydrogen sulfate as a dual-functional catalyst
  7. Efficient synthesis of pyrido[2,3-d]pyrimidine-7-carboxylic acids catalyzed by a TiO2/SiO2 nanocomposite in aqueous media at room temperature
  8. Synthesis, characterization, and antitumor activity of some novel S-functionalized benzo[d]thiazole-2-thiol derivatives; regioselective coupling to the –SH group
  9. A zinc(II) coordination polymer containing single- and double-stranded helical chains: synthesis, crystal structure, and thermal and luminescence properties
  10. An unexpected lanthanum chloride carbonate hydrate: synthesis, crystal structure, vibrational spectra and thermal degradation of LaCl[CO3]·3H2O
  11. Structures of the diiodine adducts of bis(diisopropylphosphano)methane disulfide and bis(diisopropylphosphano)ethane disulfide
  12. Note
  13. Photoluminescence of Baltic amber
https://doi.org/10.1515/znb-2018-0064
Keywords for this article
1,2-dihydropyridine-2-thiones; 2-phenacyl-1,3,4-thiadiazoles; condensation reactions; orthoamides of alkyne carboxylic acids; push-pull-substituted butadienes

Articles in the same Issue

  1. Frontmatter
  2. In this Issue
  3. NQR, NMR, and X-ray crystal structure studies of [4-C2H5-C6H4NH3]2MBr4 (M=Zn, Cd)
  4. Ein ökonomisches Verfahren zur Aufarbeitung von Reaktionsgemischen bei Lewis-Säure-induzierten elektrophilen Aromatensubstitutionen
  5. Orthoamide und Iminiumsalze, XCIVa. Kondensationsreaktion von Orthoamiden von Alkincarbonsäuren mit 2-Methyl-5-phenacyl-1,3,4-thiadiazolen
  6. Highly effectual synthesis of 4,6-diarylpyrimidin-2(1H)-ones using N,N,N′,N′-tetramethylethylenediaminium-N,N′-disulfonic acid hydrogen sulfate as a dual-functional catalyst
  7. Efficient synthesis of pyrido[2,3-d]pyrimidine-7-carboxylic acids catalyzed by a TiO2/SiO2 nanocomposite in aqueous media at room temperature
  8. Synthesis, characterization, and antitumor activity of some novel S-functionalized benzo[d]thiazole-2-thiol derivatives; regioselective coupling to the –SH group
  9. A zinc(II) coordination polymer containing single- and double-stranded helical chains: synthesis, crystal structure, and thermal and luminescence properties
  10. An unexpected lanthanum chloride carbonate hydrate: synthesis, crystal structure, vibrational spectra and thermal degradation of LaCl[CO3]·3H2O
  11. Structures of the diiodine adducts of bis(diisopropylphosphano)methane disulfide and bis(diisopropylphosphano)ethane disulfide
  12. Note
  13. Photoluminescence of Baltic amber
Sign up now to receive a 20% welcome discount
Institutional Access
How does access work?
Have an idea on how to improve our website?
Please write us.
© 2025 De Gruyter Brill
Downloaded on 27.9.2025 from https://www.degruyterbrill.com/document/doi/10.1515/znb-2018-0064/html
Scroll to top button