Scalable Synthesis of Silacyclohexanones and Ready Access to Silicon Building Blocks
Eagala Ramesh1, Laxman D Nandawadekar1,2, Ramana Sreenivasa Rao3
1Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad, 500007, India.
Organic Letters
|September 8, 2023
Summary
A novel two-step synthesis creates silicon-containing cyclohexanone derivatives. These compounds are then converted into diverse silicon-infused heterocycles, including a potential HDAC6 inhibitor analogue.
Area of Science:
- Organic Chemistry
- Organosilicon Chemistry
- Medicinal Chemistry
Background:
- Organosilicon compounds offer unique properties for materials and pharmaceuticals.
- Developing efficient synthetic routes to novel silicon heterocycles is crucial.
- Silacyclohexanone scaffolds are valuable intermediates in organic synthesis.
Purpose of the Study:
- To present a simple and efficient two-step method for synthesizing silacyclohexanones.
- To explore the transformation of these silacyclohexanones into various silicon-containing heterocycles.
- To synthesize a sila-analogue of the HDAC6 inhibitor tubastatin A.
Main Methods:
- Synthesis of silacyclohexanones from bis(bromoethylsilanes) using TosMIC (Tosylmethyl isocyanide).
- Subsequent chemical transformations of the synthesized silacyclohexanones.
- Application of the methodology for targeted synthesis of a tubastatin A analogue.
Main Results:
- A straightforward two-step synthesis for silacyclohexanones was established.
- Nine distinct silicon-containing heterocycles were successfully prepared.
- A sila-analogue of tubastatin A was synthesized, demonstrating the method's utility.
Conclusions:
- The developed method provides an efficient route to silacyclohexanones and their derived heterocycles.
- This methodology expands the scope of organosilicon heterocycle synthesis.
- The approach is applicable to the synthesis of potential pharmaceutical agents.
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