89201-19-4Relevant academic research and scientific papers
Reactions of cyclohexyl isocyanide, dialkyl acetylenedicarboxylates and 1-aryl-2-ene-3-acetyl-1,4-diketones: One-pot synthesis of highly functionalized 5-cyclohexylimino-2,5-dihydrofurans
Latifi, Mahsa,Talebdizaeh, Mahdiyeh,Anary-Abbasinejad, Mohammad
, p. 66 - 72 (2018/10/26)
Dihydrofurans are important intermediates in organic synthesis, and are also important starting materials used in syntheses of a number of natural products. A facile synthesis of highly functionalized 5- cyclohexylimino-2,5-dihydrofuran derivatives by the multi-component reaction of cyclohexyl isocyanide, dialkyl acetylenedicarboxylates and 1-aryl-2-ene-3-acetyl-1,4-diketones is described.
Photooxygenation of 3-acetyl-5-aryl-2-methylfurans via endoperoxide intermediate and the following reactions
Onitsuka, Satoaki,Nishino, Hiroshi,Kurosawa, Kazu
, p. 6003 - 6009 (2007/10/03)
The photooxygenation of 3-acetyl-5-aryl-2-methylfurans 1a-e selectively produced 2,2-diacetyl-3-aroyloxiranes 2a-e, 3-acetyl-1-aryl-2-pentene-1,4-diones 3a-e, and 3-acetyl-1-aryl-2-hydroxy-2-pentene-1,4-diones 4a-d via the endoperoxide intermediate A depending on the reaction conditions and the work-up procedure. The oxiranes 2a-e were mainly obtained in 56-77% yields by allowing the reaction mixture to stand at ambient temperature after the irradiation, while the treatment of the reaction mixture with water mainly gave the 1,4-diones 3a-e (62-69%). Heating the reaction mixture at 80°C after the irradiation decreased the total yield of the products, however, the enols 4a-d were newly formed in 8-12% yields. Direct UV irradiation of the endoperoxide intermediate A led to the homolytic fission of the peroxide linkage to produce the same enols 4a-e (16-39%). The self-sensitized photooxygenation of 1a-d using a UV light also gave 4a-d in a similar yield. The reaction pathway is discussed based on these results.
