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An efficient route to pyrimidine nucleoside analogues by [4 + 2] cycloaddition reaction
Morwenna S M Pearson1, Aélig Robin, Nathalie Bourgougnon
1Laboratoire de Synthèse Organique, UMR CNRS 6513, Faculté des Sciences et des Techniques, 2, Rue de la Houssinière 44322 Nantes 03, France.
The Journal of Organic Chemistry
|October 25, 2003
Summary
This study presents an efficient synthesis of pyrimidine nucleoside analogues using a [4 + 2] cycloaddition reaction. The method yields beta-D-uracil analogues with high regiocontrol from readily available starting materials.
Area of Science:
- Organic Chemistry
- Medicinal Chemistry
- Synthetic Chemistry
Background:
- Pyrimidine nucleoside analogues are important in medicinal chemistry.
- Efficient synthetic routes are crucial for developing new analogues.
Purpose of the Study:
- To develop an efficient synthesis for pyrimidine nucleoside analogues.
- To utilize a [4 + 2] cycloaddition reaction for heterocyclic synthesis.
Main Methods:
- Convergent synthesis involving glycosyl isothiocyanates and a diazadienium salt.
- Preparation of diazapentadienium iodide from vinylthioamide.
- Reaction of isothiocyanates with the diazadienium salt.
Main Results:
- Synthesis of beta-D-uracil analogues (7a-f) in good yields.
- Demonstration of total regiocontrol in the cycloaddition reaction.
- Characterization of all synthesized compounds using IR, HRMS, and NMR (COSY, HMQC).
Conclusions:
- The reported [4 + 2] cycloaddition provides an efficient route to pyrimidine nucleoside analogues.
- Diazapentadienium iodide is an effective intermediate for heterocyclic synthesis.
- The method offers a valuable tool for accessing novel beta-D-uracil derivatives.