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Synthesis of novel benzo[6,7]cyclohepta[1,2-b]thieno[3,2-e]pyridines and their bis-analogues linked to different spacers: Approach to a new ring system.
- Source :
- Synthetic Communications; Oct2023, Vol. 53 Issue 20, p1701-1712, 12p, 6 Diagrams, 3 Charts, 2 Graphs
- Publication Year :
- 2023
-
Abstract
- The synthesis of benzosuberone-fused heterocyclic derivatives is an increasingly intriguing subject. The current study reports the synthesis of the new ring system benzo[6,7]cyclohepta[1,2-b]thieno[3,2-e]pyridine. At first, new 2-thioxo-2,5,6,7-tetrahydro-1H-benzo[6,7]cyclohepta[1,2-b]pyridine-3-carbonitriles were prepared and taken as versatile precursors for the present study. Afterward, a succession of α-bromoketones were combined with the newly generated synthons in ethanol that also included two equivalents of sodium ethoxide. After 2–3 h of heating at reflux, a novel series of benzo[6,7]cyclohepta[1,2-b]thieno[3,2-e]pyridines was obtained in 86–93% yields. Using a similar protocol, a novel series of benzosuberone-fused bis(thieno[3,2-e]pyridines) linked to different spacers was obtained. Therefore, two pyridine-2(1H)-thiones equivalents were reacted with one equivalent of the respective bis(α-bromoketones) in ethanol containing four equivalents of sodium ethoxide. The reaction mixture was refluxed for 4–6 h to produce the corresponding bis(benzo[6,7]cyclohepta[1,2-b]thieno[3,2-e]pyridines) in 67–76% yields. Both spectral data and elemental analyses were used to elucidate the structure of new products. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00397911
- Volume :
- 53
- Issue :
- 20
- Database :
- Complementary Index
- Journal :
- Synthetic Communications
- Publication Type :
- Academic Journal
- Accession number :
- 171952164
- Full Text :
- https://doi.org/10.1080/00397911.2023.2241584