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Multicomponent synthesis of spiro 1,3,4‐thiadiazolines with anticancer activity by using deep eutectic solvent under microwave irradiation

2022; Wiley; Volume: 60; Issue: 3 Linguagem: Inglês

10.1002/jhet.4591

1943-5193

Aleff Castro, Isadora Maria Gouveia Andrade, Maísa Cavalcanti Coelho, Daniel P. Costa, Dayse N. Moreira, Rachel Azevedo Maia, Gesiane da Silva Lima, Gabriel Franco dos Santos, Boniek G. Vaz, Gardênia Carmen Gadelha Militão, Paulo Bruno Norberto da Silva, Mário Luiz Araújo de Almeida Vasconcellos, Cláudio Gabriel Lima-Júnior,

Sulfur-Based Synthesis Techniques

Abstract This work describes a simple and efficient alternative method for obtaining 1,3,4‐thiadialzolinic spirocompounds, combining the use of deep eutectic solvents (DES) with microwave irradiation in a one‐pot process. A series of DES based on different acids was explored as a solvent in a three‐component reaction including isatin derivatives (monomeric and dimeric), thiosemicarbazide, and acetic anhydride. Choline chloride and oxalic acid (1:1) showed better results concerning the other solvents evaluated, reaching yields of up to 79% when applied to the other compounds of the proposed series. For most of the monomeric compounds, the yields were very close to or higher than those reported in the literature for two‐step synthesis. These results demonstrate the possibility of using one‐pot synthesis as a faster, cleaner, and more efficient alternative method for obtaining thiadiazolines with expressive cytotoxic activity.