Synthesis and reduction of thieno[2′,3′(3′,2′ or 3′,4′):5,6]-azocino[2,1-a]isoindole-7, 13-diones
✍ Scribed by Mohamed Othman; Pascal Pigeon; Bernard Decroix
- Publisher
- Journal of Heterocyclic Chemistry
- Year
- 1998
- Tongue
- English
- Weight
- 353 KB
- Volume
- 35
- Category
- Article
- ISSN
- 0022-152X
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✦ Synopsis
Abstract
A synthesis of the thieno[2′,3′(3′,2′ or 3′,4′):5,6]azocino[2,1‐a]isoindole‐7,13‐diones 6a‐c was developed from N‐thienylethylphthalimides 3a‐c using a Wittig reaction followed by a Friedel‐Crafts cyclization of acetic acid derivatives 5a‐c. Reduction of ketones 6a‐c into alcohols 7a‐c was stereo specific.
📜 SIMILAR VOLUMES
In the title compound, C 16 H 13 Cl 3 N 2 O 3 S, the 1,3-thiazole ring is almost orthogonal to the isoindoline plane, making a dihedral angle of 89.74 (9) . Intermolecular O-HÁ Á ÁN and C-HÁ Á ÁO interactions and SÁ Á ÁO short contacts link the molecules into a three-dimensional framework. The cryst
## Abstract Cyclization of thioglycolic acids derivatives 3a‐d gave isoindolo[1,2‐__b__]thieno[2,3(3,2 or 3,4)‐__e__][1,3]‐thiazocines 4a‐d. Isoindolo[2,1‐__a__]thieno[2,3(3,2 or 3,4)‐__f__][1,4] or [1,5]diazocines 10b or 11a‐c were synthesized from Beckmann or Schmidt rearrangement of the ketones
## Abstract magnified image An efficient one‐pot access for the synthesis of the previously unreported tetracyclic fused pyrimido‐[4″,5″:4′,5′]thieno[3′,2′:4,5]thieno[3,2‐__d__]pyrimidine (**3**) and 1,2,3‐triazine[4″,5″:4′,5′]thieno‐[3′,2′:4,5]thieno‐[3,2‐__d__]‐1,2,3‐triazine (**5**) heteroaroma