- Three-component access to 2-pyrrolin-5-ones and their use in target-oriented and diversity-oriented synthesis
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The Hantzsch-type microwave-assisted, solvent-free sequential three-component reaction between primary amines, β-dicarbonyl compounds and α-bromoesters in the presence of indium trichloride afforded 2-pyrrolin-5-ones, which are difficult to access by alternative methods. Ready access to these compounds allowed their use as synthetic building blocks in a target-oriented project aimed at the synthesis of a compound that had previously been postulated as a candidate for HIV integrase inhibition on the basis of computational studies. The versatility of 2-pyrrolin-5-ones was further verified by their use in a diversity-oriented synthesis context, leading to a library of highly functionalized bispiro compounds. The overall process leading to these compounds involved the generation of six bonds and two cycles over three steps, two of which are multicomponent, and the fully controlled generation of up to four stereocenters, including two quaternary ones.
- Cores, ángel,Estévez, Verónica,Villacampa, Mercedes,Menéndez, J. Carlos
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p. 39433 - 39443
(2016/06/01)
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- New approaches to polysubstituted pyrroles and pyrrolinones from α-cyanomethyl-β-ketoesters
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In this present paper, we report the efficient, regioselective one-pot synthesis of 5-alkoxy and 5-alkylsulfanylpyrrole-3-carboxylates in high yields via the zinc perchlorate-catalyzed addition of alcohols and thiols to the nitrile carbon of α-cyanomethyl
- Demir, Ayhan S.,Emrullahoglu, Mustafa,Ardahan, Gülben
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p. 461 - 468
(2007/10/03)
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- Reactivity and microbiological activity of 2-methyl-3-carboethoxy-5-pyrrolinone derivatives
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This work describes the synthesis of 2-methyl-3-carboethoxy-5-pyrrolinone which was then allowed to react with aromatic aldehydes, nitromethines, benzendiazonium salts, hydrazine and amines. Several of the products have shown good results in preliminary antimicrobial and antifungal tests.
- Lovren,Gaon,Bobarevic
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p. 773 - 776
(2007/10/02)
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