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Synlett 2012(4): 632-636
DOI: 10.1055/s-0031-1290347
DOI: 10.1055/s-0031-1290347
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
Ugi-Smiles Coupling of Thiouracil Derivatives towards 2,4-Diamino Pyrimidines
Further Information
Received
4 November 2011
Publication Date:
10 February 2012 (online)
Publication History
Publication Date:
10 February 2012 (online)
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Abstract
Diaminopyrimidines could be synthesized via a multicomponent coupling starting from S-alkyl thiouracil derivatives. The synthetic strategy based upon an Ugi-Smiles coupling, and subsequent oxidation of the adducts affords a versatile platform for the preparation of various diaminopyrimidines with five points of diversity. The whole sequence may be performed as a one-pot process.
Key words
Ugi-Smiles - thiouracil - isocyanide - diaminopyrimidines - SNAr
- Supporting Information for this article is available online:
- Supporting Information
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References and Notes
All previous reported Ugi-Smiles couplings of pyrimidines have only been performed on monohydroxy or mono-mercapto derivatives,6 as a second electron-donating group was expected to lower the efficiency of the Smiles step.