Synthesis of 3-alkyl-5-allylamino-2-benzoylimino-1,3,4-thiadiazoles via Dimroth rearrangement

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Abstract: A facile access to 3-alkyl-5-N-allylamino-2-N′-benzoylimino-1,3,4-thiadiazoles via Dimroth rearrangement is reported. Alkylation of 5-allylamino-4-benzoyl-1,2,4-triazole-3-thione with alkyl halides in basic alcohol solution is regioselective. A mechanism for the formation of a 1,3,4-thiadiazole ring by 1,2,4-triazole recyclization is proposed. The obtained compounds were characterized by NMR, elemental analysis and X-ray diffraction analysis.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Synthesis of 3-alkyl-5-allylamino-2-benzoylimino-1,3,4-thiadiazoles via Dimroth rearrangement ; volume:22 ; number:2 ; year:2016 ; pages:79-83 ; extent:5
Heterocyclic communications ; 22, Heft 2 (2016), 79-83 (gesamt 5)

Creator: Fizer, Maksym
Slivka, Mikhailo
Baumer, Vjacheslav
Lendel, Vasil

DOI: 10.1515/hc-2015-0279

URN: urn:nbn:de:101:1-2501130618063.641357747419

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:28 AM CEST

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Fizer, Maksym
Slivka, Mikhailo
Baumer, Vjacheslav
Lendel, Vasil

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Synthesis of 3-alkyl-5-allylamino-2-benzoylimino-1,3,4-thiadiazoles via Dimroth rearrangement

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Other Objects (12)

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IMPROVED SYNTHESIS OF UNSYMMETRICAL UREAS VIA N-ALKYL CARBAMATES

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