Base Mediated Diazirination via Iodine(III) Reagents
Monish Arbaz Ansari1, Ganesh Kumar1, Maya Shankar Singh1
1Department of Chemistry, Institute of Science, Banaras Hindu University, Varanasi 221 005, India.
This study introduces a new method to create functionalized diazirines using carbohydrazides and hypervalent iodine reagents. This efficient process works under mild conditions and is applicable to various molecules, including biologically relevant compounds.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Diazirines are versatile synthetic intermediates.
- Efficient methods for diazirine synthesis are crucial for organic chemistry.
Purpose of the Study:
- To develop an efficient and practical method for synthesizing highly functionalized diazirines.
- To demonstrate the broad applicability of the developed method.
Main Methods:
- Reaction of carbohydrazides with diazo-substituted hypervalent iodine reagents.
- Utilizing user-friendly and easily practicable reaction conditions.
Main Results:
- Successful synthesis of diverse diazirine derivatives.
- Demonstrated applicability to various substrates including d-glucose, menthol, aspirin, proline, and lithocholic acid.
- The method is mild, robust, and highly selective for aryl, alkyl, benzyl, and heterocyclic hydrazides.
Conclusions:
- The developed method provides an efficient route to functionalized diazirines.
- The reaction is mild, selective, and broadly applicable to complex molecules.
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