Synthesis of Oxopyrazolidine-1-carboximidamides from Morita Baylis-Hillman adducts

Synthesis of Oxopyrazolidine-1-carboximidamides from Morita Baylis-Hillman adducts

Jr., Manoel T. Rodrigues; Correia, José Tiago M.; Coelho, Fernando

Abstract:

Pyrazolidin-3-ones derivatives, including 5- oxopyrazolidine-1-carboximidamides, are an important class of compounds, which possess widespread pharmacological properties such as analgesic, antipyretic and anticancer. Several synthetic approaches have been developed to access pyrazolidin-3-one rings. In this work we disclose a facile and diastereoselective synthetic approach to prepare oxopyrazolidine-1- carboximidamides derivatives from Morita-Baylis- Hillman (MBH) adducts. Our approach is based on a tandem sequence involving a Michael addition reaction and cyclization, which forms in a single step a new cycle and controls the relative stereochemistry of two centers.

Pyrazolidin-3-ones derivatives, including 5- oxopyrazolidine-1-carboximidamides, are an important class of compounds, which possess widespread pharmacological properties such as analgesic, antipyretic and anticancer. Several synthetic approaches have been developed to access pyrazolidin-3-one rings. In this work we disclose a facile and diastereoselective synthetic approach to prepare oxopyrazolidine-1- carboximidamides derivatives from Morita-Baylis- Hillman (MBH) adducts. Our approach is based on a tandem sequence involving a Michael addition reaction and cyclization, which forms in a single step a new cycle and controls the relative stereochemistry of two centers.

Palavras-chave:

DOI: 10.5151/chempro-14bmos-R0303-1

Referências bibliográficas

• [1] 1Gadad, A. K.; Mahajanshetti, C. S.; Nimbalkar, S.; Raichurkar, A. Eur. J. Med. Chem. 2000, 35, 853.
• [2] 2 Coelho, F.; Almeida, W. P.; Mateus, C. R.; Feltrin, M.; Costa, A. M. Tetrahedron 2001, 57, 6901.
• [3] 3. Rodrigues Jr., M. T.; Gomes, J. C.; Smith, J.; Coelho, F. Tetrahedron Lett. 2010, 51, 4988.

Como citar:

Jr., Manoel T. Rodrigues; Correia, José Tiago M.; Coelho, Fernando; "Synthesis of Oxopyrazolidine-1-carboximidamides from Morita Baylis-Hillman adducts", p-303-303. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0303-1