A simple approach to symmetrical and unsymmetrical ureas

A simple approach to symmetrical and unsymmetrical ureas

Viana, G. M.; Ferrão, J. A.; Senra, J. D.; Vasconcelos, M. G.; Simas, A. B. C.; Aguiar, L. C. S.

Abstract:

Mild and efficient methods for the synthesis of substituted ureas have continued to attract a widespread interest for a long time due to their diverse biological activity. Here we wish to report a new facile methodology to prepare substituted ureas, just treating their respective thioureas with aqueous potassium dichloroiodate (KICl2). An interesting oxidation reaction in organic chemistry is the oxidation of thioureas. Depending on the oxidizing agent, reaction conditions and the substitution pattern of thioureas, a variety of products have been isolated. Different from the literature reports dealing with methodologies describing that thioureas can be transformed into ureas (lead tetraacetate; oxone; manganese dioxide; tetrabutylammonium perio-date), our approach also allows the simultaneous synthesis of iodinated aryl-ureas.

Mild and efficient methods for the synthesis of substituted ureas have continued to attract a widespread interest for a long time due to their diverse biological activity. Here we wish to report a new facile methodology to prepare substituted ureas, just treating their respective thioureas with aqueous potassium dichloroiodate (KICl2). An interesting oxidation reaction in organic chemistry is the oxidation of thioureas. Depending on the oxidizing agent, reaction conditions and the substitution pattern of thioureas, a variety of products have been isolated. Different from the literature reports dealing with methodologies describing that thioureas can be transformed into ureas (lead tetraacetate; oxone; manganese dioxide; tetrabutylammonium perio-date), our approach also allows the simultaneous synthesis of iodinated aryl-ureas.

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DOI: 10.5151/chempro-14bmos-R0338-1

Referências bibliográficas

• [1] 1 Garden, S. J. et al, Tetrahedron Letters, 2001, 42, 2089.
• [2] 2 Debroy, A, et al, Bull. Chem. Soc. Jpn., 1984, 57, 315.
• [3] 3 Mohammadpoor-Baltork, I. et al, Synthetic Communications, 2003, 953.
• [4] 4 Sharma, T. C. et al, Bull. Chem. Soc. Jpn., 1978, 51, 1245.
• [5] 5 Pourali, A. R. et al, Monatshefte fuer Chemie, 2005, 136, 733.
• [6] 6 Senra, J. D.; Malta, L. F. B.; Michel, R. C.; da Costa, M. E. H. M.; Aguiar, L. C. S.; Simas, A. B. C.; Antunes, O. A. C. Adv. Synth. Catal., 2009, 351, 2411.

Como citar:

Viana, G. M.; Ferrão, J. A.; Senra, J. D.; Vasconcelos, M. G.; Simas, A. B. C.; Aguiar, L. C. S.; "A simple approach to symmetrical and unsymmetrical ureas", p-338-338. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0338-1