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1.
Org Biomol Chem ; 21(35): 7209-7218, 2023 Sep 13.
Artigo em Inglês | MEDLINE | ID: mdl-37642476

RESUMO

We have discovered that three molecules of arylacetylene are rapidly (15 min) assembled with one molecule of nitrile at room temperature in the KOBut/DMSO system to afford 2-aryl-3-arylethynyl-4-aryl-5-benzyl-1H-pyrroles in up to 76% yield. We assume that this unprecedented self-organization process involves the cascade addition of acetylenic carbanions, first to the CN, then to the CC and CC bonds of the intermediates, followed by pyrrole ring closure via the intramolecular nucleophilic addition of the NH functional group to the CC bond of the final intermediates.

2.
Org Biomol Chem ; 20(33): 6593-6605, 2022 08 24.
Artigo em Inglês | MEDLINE | ID: mdl-35920307

RESUMO

Pure (E)-alkenoyl dihydropyrans are stereoselectively assembled from 2-acetyl-3,4-dihydropyrans (products of one-pot self-organization of acetylene gas and ketones) and aromatic aldehydes (52-86% yields). Furthermore, (E)-alkenoyl dihydropyrans undergo ring opening (acid hydrolysis) to afford 5-hydroxy-1,6-diketones (44-67% yields) and acetyl-2-(E)-styryl-2,3-dihydroxycyclopentanes (19-32% yields), both as single diastereomers.


Assuntos
Acetileno , Cetonas , Ciclopentanos , Estrutura Molecular , Estereoisomerismo
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