Preparation of 3-aminoalkylbenzo[b]thiophenes
✍ Scribed by Frank Burkamp; Stephen R. Fletcher
- Publisher
- Journal of Heterocyclic Chemistry
- Year
- 2002
- Tongue
- English
- Weight
- 109 KB
- Volume
- 39
- Category
- Article
- ISSN
- 0022-152X
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✦ Synopsis
Abstract
We report an efficient entry into substituted 3‐(ω‐aminoalkyl)‐benzo[b]thiophenes that allows rapid generation of structural diversity. Alkylation of α,ω‐dihaloketones with thiophenols followed by acid‐catalysed cyclisation led to an efficient synthesis of 3‐(ω‐aminoalkyl)benzo[b]thiophenes. 2‐Carboethoxy derivatives were prepared using a directed ortho‐metallation approach. These derivatives were readily converted into the corresponding amines.
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Synthesis of Polyfunctionalized Thiophenes and Enediynes via Ring-Opening Reactions of 3-Lithiated Thieno[2,3-b](and [3,2b])thiophenes , 3,4-Dilithiated Thieno[2,3-b]thiophenes and3,6-Dilithiated Thieno[3,2-b]thiophenes. -Solutions of title lithiated thienothiophenes are obtained from the correspond
## Abstract An efficient one pot access to variously substituted thieno[2,3‐__b__]thiophene is described. The title compounds were obtained from 1,3‐dicarbonyl or equivalent compounds, carbon disulfide and halomethyl derivatives in good to high yields and fully characterized.
Rust) 160 (calc. 165.2); Amax= 247mp (log€ = 3.89);222mp (log E = 4.38) [3]) is obtained in 79 % yield.