Multicomponent synthesis of R-(+)-limonene-based 1,3,4-thiadiazoles

Multicomponent synthesis of R-(+)-limonene-based 1,3,4-thiadiazoles

Falzirolli, Hugo; Vandresen, Fábio; Furlan, Francieli; Silva., Cleuza Conceição da

Abstract:

1,3,4-thiadiazoles find application in several areas of modern chemistry and, for this reason, improvements on their synthesis are constantly sought. The oxidative cyclization involving thiosemicarbazones in the presence of oxidizing agent such as ferric ions lies among the common strategies for the synthesis of this five-membered ring. Improvements on this method have led to successful one-pot and solid-phase syntheses of 1,3,4-thiadiazoles. Looking for biological active molecules, our research group works on semi-synthesis of compounds bearing terpenic moiety. Attempting not only to obtain new terpenic 1,3,4- thiadiazoles but also optimize their synthesis, an efficient multicomponent method is reported herein, where the cyclization takes place directly from the thiosemicarbazide of R-(+)-limonene, aldehyde and the iron(III) chloride.

1,3,4-thiadiazoles find application in several areas of modern chemistry and, for this reason, improvements on their synthesis are constantly sought. The oxidative cyclization involving thiosemicarbazones in the presence of oxidizing agent such as ferric ions lies among the common strategies for the synthesis of this five-membered ring. Improvements on this method have led to successful one-pot and solid-phase syntheses of 1,3,4-thiadiazoles. Looking for biological active molecules, our research group works on semi-synthesis of compounds bearing terpenic moiety. Attempting not only to obtain new terpenic 1,3,4- thiadiazoles but also optimize their synthesis, an efficient multicomponent method is reported herein, where the cyclization takes place directly from the thiosemicarbazide of R-(+)-limonene, aldehyde and the iron(III) chloride.

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DOI: 10.5151/chempro-15bmos-BMOS2013_2013821151948

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Como citar:

Falzirolli, Hugo; Vandresen, Fábio; Furlan, Francieli; Silva., Cleuza Conceição da; "Multicomponent synthesis of R-(+)-limonene-based 1,3,4-thiadiazoles", p-195-195. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-BMOS2013_2013821151948