A novel transformation of β-1,2,3-thiadiazol-5-yl enamines into thieno[2,3-d]pyridazines / Rozin Y., Zhidovinov S., Beryozkina T., Shafran Y., Lubec G., Eltsov O., Slepukhin P., Knippschild U., Bischof J., Dehaen W., Bakulev V. // Tetrahedron Letters. - 2015. - V. 56, l. 12. - P. 1545-1547.

ISSN:
00404039
Type:
Article
Abstract:
Reactions of β-1,2,3-thiadiazol-5-yl enamines with acetyl chloride in 1,4-dioxane lead to the formation of either dienamines or novel thieno[2,3-d]pyridazines depending on the time and reaction temperature. Conditions were found for the selective synthesis of thieno[2,3-d]pyridazines. A plausible mechanism involves formation of C-S and C-C bonds and a novel ring rearrangement of 5-vinyl-1,2,3-thiadiazoles into pyridazine-4-thiolates. A series of new diamides of 2-(4-carboxy-1,2,3-thiadiazol-5-yl)thieno[2,3-d]pyridazine-7-carboxylic acid is prepared by reaction of the methyl ester with primary and secondary amines. © 2015 Elsevier Ltd. All rights reserved.
Author keywords:
Enamines; Rearrangement; Thiadiazoles; Thieno[2,3-d]pyridazines; Transformation
Index keywords:
antibiotic agent; checkpoint kinase 1; checkpoint kinase 2; chloride; dioxane; enamine; hydrogen; pyridazine derivative; amidation; antiarrhythmic activity; antiasthmatic activity; antiinflammatory ac
DOI:
10.1016/j.tetlet.2015.02.013
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Affiliations TOS Department, Ural Federal University Named after the First President of Russia B.N. Yeltsin, 19 Mira Str., Yekaterinburg, Russian Federation; Medical University of Vienna, Department of Pediatrics, 14 Lazarettgasse, Vienna, Austria; I.Ya. Postovsky Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences, 20 S. Kovalevskaya Str., Ekaterinburg, Russian Federation; Klinik für Allgemein-und Viszeralchirurgie, Zentrum für Chirurgie, Universitätsklinikum Ulm, 23 Albert-Einstein-Allee, Ulm, Germany; Molecular Design and Synthesis, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, Leuven, Belgium
Author Keywords Enamines; Rearrangement; Thiadiazoles; Thieno[2,3-d]pyridazines; Transformation
Chemicals/CAS checkpoint kinase 2, 244634-79-5; chloride, 16887-00-6; dioxane, 123-91-1; hydrogen, 12385-13-6, 1333-74-0
Funding Details 14-03-01033, RFBR, Russian Foundation for Basic Research
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Correspondence Address Beryozkina, T.; TOS Department, Ural Federal University Named after the First President of Russia B.N. Yeltsin, 19 Mira Str., Russian Federation
Publisher Elsevier Ltd
CODEN TELEA
Language of Original Document English
Abbreviated Source Title Tetrahedron Lett.
Source Scopus