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Accessing the Rare Diazacyclobutene Motif
Chandima J Narangoda1, Timothy R Lex1, Madelyn A Moore1
1Department of Chemistry , Clemson University , Clemson , South Carolina 29634 , United States.
Organic Letters
|December 12, 2018
Summary
A new [2+2] cycloaddition reaction efficiently synthesizes diazacyclobutenes using 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) and alkynyl sulfides/selenides. This method offers a versatile route to a rare class of heterocyclic compounds.
Area of Science:
- Organic Chemistry
- Heterocyclic Chemistry
Background:
- 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) is a reactive dienophile.
- Accessing diazacyclobutenes is challenging.
- Alkynyl sulfides and selenides offer unique reactivity.
Purpose of the Study:
- To develop a novel [2+2] cycloaddition reaction.
- To synthesize diazacyclobutenes from alkynyl sulfides and selenides.
- To explore the scope and limitations of this new synthetic method.
Main Methods:
- Formal [2+2] cycloaddition reaction.
- Use of 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD).
- Substrates included electron-rich alkynyl sulfides and selenides.
Main Results:
- Efficient synthesis of diazacyclobutenes achieved in good yields.
- Broad substrate scope demonstrated for thio-acetylenes.
- A unique and rarely accessible class of heterocycles is now accessible.
Conclusions:
- The developed [2+2] cycloaddition provides a convenient method for diazacyclobutene synthesis.
- The reaction tolerates a wide range of alkynyl sulfides and selenides.
- Further studies involving dynamic NMR, X-ray crystallography, and computation are needed to understand the scaffold's aromaticity.
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