Synthesis and stereochemistry of 3-acetyl-5-aminospiro[1,3,4-thiadiazoline- 2,4′-thioflavans]

László Somogyi, Gyula Batta, Tamás E. Gunda, Attila Cs Bényei

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Abstract

(Chemical Equation Presented) Under acetylating conditions racemic thioflavanone thiosemicarbazones cyclize into racemic 3-acetylspiro[1,3,4- thiadiazoline-2,4′-thioflavans] and a racemic 3-acetylspiro[1,3,4- oxadiazoline-2,4′-thioflavan] with trans O(1) or S(1) and Ph(2′eq). Hindered rotation of the endocyclic N(3) acetyl group spirothiadiazolines caused the formation of isomers separable by HPLC. X-ray diffraction analyses, 1H-, 13C-, and 15N NMR measurements as well as MOPAC QM calculations were performed to reveal the structures of these isomers.

Original languageEnglish
Pages (from-to)489-495
Number of pages7
JournalJournal of Heterocyclic Chemistry
Volume45
Issue number2
DOIs
Publication statusPublished - Jan 1 2008

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ASJC Scopus subject areas

  • Organic Chemistry

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