Unexpected reactions of dithiodiglycolic acid: isolation of a novel seven-membered ring system based on a 2-amino derivative of 7-oxo-6,7-dihydro-[1,4,5]oxadithiepine
✍ Scribed by Min Li; Robert S Wu; Jane Tsai; Salvatore J Salamone
- Book ID
- 104251340
- Publisher
- Elsevier Science
- Year
- 2002
- Tongue
- French
- Weight
- 123 KB
- Volume
- 43
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
A novel seven-membered ring was unexpectedly isolated from the coupling of dithiodiglycolic acid with 2.2 equiv. of N-hydroxysuccinimide, followed by addition of 0.25 equiv. of methyl (4-aminomethyl)benzoate hydrochloride (2) in the presence of 2 equiv. of triethylamine.
📜 SIMILAR VOLUMES
The title compound, C 10 H 14 N 4 O 3 S, is the first example of the fused tricyclic octahydro-1-thia-2,3a,8a-triazacyclopenta[a]indene ring system. The S-containing heterocycle adopts a typical envelope conformation, fused at the 2,3-positions to a 2,3a,4,5,6,7-hexahydroindazol-3-one unit.
In the paper by Liepa, Jahangiri, Fallon & Forsyth [Acta Cryst. (2006), E62, o3170-o3171], there is an error in the reaction scheme. The correct scheme is given below.