Microwave-assisted synthesis of fused tetrazoleketopiperazine compounds via Ugi reactions

Microwave-assisted synthesis of fused tetrazoleketopiperazine compounds via Ugi reactions

Amaral, André Felipe C.; Silva, Wender A.; Andrade, Carlos Kleber Z.

Abstract:

Multicomponent Reactions (MCRs) offer many advantages, and due to their ability to rapidly create molecular diversity and molecular complexity, allowing the generation of compounds containing essentially all the atoms of the reactants, they have become an important way to synthesize novel bioactive products. The classical Ugi four-component (U-4CR) reaction is one of the most known multicomponent reaction, in which an isocyanide, an aldehyde or ketone, a carboxylic acid and an amine combine to yield α- acylamino amides. We report herein a concise way to synthezise compounds containing both the tetrazole and ketopiperazine nuclei as synergistic moieties via a modified Ugi reaction in which the acid has been replaced by trimethylsilylazide (TMSN3). Tetrazoles and ketopiperazines are important heterocycles and both have interest in the pharmaceutical industry.

Multicomponent Reactions (MCRs) offer many advantages, and due to their ability to rapidly create molecular diversity and molecular complexity, allowing the generation of compounds containing essentially all the atoms of the reactants, they have become an important way to synthesize novel bioactive products. The classical Ugi four-component (U-4CR) reaction is one of the most known multicomponent reaction, in which an isocyanide, an aldehyde or ketone, a carboxylic acid and an amine combine to yield α- acylamino amides. We report herein a concise way to synthezise compounds containing both the tetrazole and ketopiperazine nuclei as synergistic moieties via a modified Ugi reaction in which the acid has been replaced by trimethylsilylazide (TMSN3). Tetrazoles and ketopiperazines are important heterocycles and both have interest in the pharmaceutical industry.

Palavras-chave:

DOI: 10.5151/chempro-15bmos-BMOS2013_2013916112849

Referências bibliográficas

• [1] 1 a) Dömling, A.; Ugi, I.; Angew. Chem. Int. Ed. 2000, 39, 3169. b)
• [2] Dömling, A.; Chem. Rev. 2006, 106, 17.
• [3] 2 Ugi I.; Fetzer, I.; Steinbrückner, C.; Angew. Chem. 1959, 71,
• [4] 386.
• [5] 3 Katritzky, A. R.; Ramsden, C. A.; Scriven, E. F. V.; Taylor, R. J.
• [6] K., Eds. In Comprehensive Heterocyclic Chemistry III, 2008,
• [7] Elsevier.

Como citar:

Amaral, André Felipe C.; Silva, Wender A.; Andrade, Carlos Kleber Z.; "Microwave-assisted synthesis of fused tetrazoleketopiperazine compounds via Ugi reactions", p-283-283. 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_2013916112849