Synthesis of new scaffolds: bisoxazolidines, thiazolidinyloxazolidines and spirothiazolidines.

Synthesis of new scaffolds: bisoxazolidines, thiazolidinyloxazolidines and spirothiazolidines.

Saiz, Cecilia; Wipf, Peter; Mahler, and Graciela

Abstract:

The discovery of new reactions and scaffolds suitable to Dynamic Combinatorial Chemistry (DCC) requires the use of different synthetic tools. Ringchain tautomerism can be applied to DCC as it involves a reversible movement of a proton accompanied by a change from an open structure to a ring. The oxygen-containing heterocycles 1, reported in the literature many years ago, have attractive biological properties which could be shared or further enhanced by the sulfur analogues. The present work describes our findings in the synthesis of thiazolidinyloxazolidine 2, the sulfur analogue of bicycle 1, as a potential DCC scaffold (Scheme 1).

The discovery of new reactions and scaffolds suitable to Dynamic Combinatorial Chemistry (DCC) requires the use of different synthetic tools. Ringchain tautomerism can be applied to DCC as it involves a reversible movement of a proton accompanied by a change from an open structure to a ring. The oxygen-containing heterocycles 1, reported in the literature many years ago, have attractive biological properties which could be shared or further enhanced by the sulfur analogues. The present work describes our findings in the synthesis of thiazolidinyloxazolidine 2, the sulfur analogue of bicycle 1, as a potential DCC scaffold (Scheme 1).

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DOI: 10.5151/chempro-14bmos-R0063-1

Referências bibliográficas

• [1] 1 Sanders, J. K. M, Otto, S. Chem. Rev. 2006, 106, 3652–3711.
• [2] 2 Audus K. L. J. Med. Chem. 2009, 52, 7537–7543.
• [3] 3 Darabantu M., Eur. J. Org. Chem. 2004, 2644-2661.
• [4] 4 Saiz, C., Wipf, P., Manta, E., Mahler, S. G. Org. Lett. 2009, 11, 3170- 3173.

Como citar:

Saiz, Cecilia; Wipf, Peter; Mahler, and Graciela; "Synthesis of new scaffolds: bisoxazolidines, thiazolidinyloxazolidines and spirothiazolidines.", p-63-63. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0063-1