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

✍ Scribed by László Somogyi; Gyula Batta; Tamás E. Gunda; Attila Cs. Bényei

Publisher
Journal of Heterocyclic Chemistry
Year
2008
Tongue
English
Weight
524 KB
Volume
45
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

magnified image

Under acetylating conditions racemic thioflavanone thiosemicarbazones cyclize into racemic 3‐acetyl‐spiro[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 spirothia‐diazolines caused the formation of isomers separable by HPLC. X‐ray diffraction analyses, ^1^H‐, ^13^C‐, and ^15^N NMR measurements as well as MOPAC QM calculations were performed to reveal the structures of these isomers.

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