878199-13-4Relevant academic research and scientific papers
Divergence in Ynone Reactivity: Atypical Cyclization by 3,4-Difunctionalization versus Rare Bis(cyclization)
Alcaide, Benito,Almendros, Pedro,Lázaro-Milla, Carlos,Delgado-Martínez, Patricia
, p. 8186 - 8194 (2018/06/15)
Functionalized ynones can be activated by Tf2C=CH2, which was generated in situ, to form zwitterionic species. These species were trapped in an intramolecular fashion by several nucleophiles to generate two major types of triflones in a divergent manner. Through fine-tuning of the reaction temperature, bis(triflyl)-6-membered- or (triflyl)-5-membered-fused-heterocycles were achieved in reasonable yields in a totally selective manner. In this way, bis(triflyl)flavones, bis(triflyl)thioflavones, bis(triflyl)selenoflavones, (triflyl)benzothienopyrans, (triflyl)benzoselenophenopyrans, (triflyl)vinyl aurones, and (triflyl)pyranoindoles were constructed. Conceivable mechanistic pathways were suggested on the basis of the isolation of several intermediates and the results from control experiments.
Pd-catalyzed selective carbonylative and non-carbonylative couplings of propiolic acid: One-pot synthesis of diarylalkynones
Kim, Wonyoung,Park, Kyungho,Park, Ahbyeol,Choe, Juseok,Lee, Sunwoo
supporting information, p. 1654 - 1657 (2013/06/26)
Diarylalkynones were synthesized from one-pot Pd-catalyzed carbonylative and noncarbonylative coupling reactions of propiolic acid with aryl iodides under a carbon monoxide atmosphere. Aryl iodide (2.0 equiv), propiolic acid (1.0 equiv), Pd(PPh3)2Cl2 (5 mol %), CuCl (10 mol %), Et3N (6.0 equiv), and CO (8 atm) were reacted under optimized conditions in CH3CN at 80 °C for 1 h. This process afforded good yields and functional group tolerance.
Diversity-oriented synthesis of 3-iodochromones and heteroatom analogues via ICl-induced cyclization
Zhou, Chengxiang,Dubrovsky, Anton V.,Larock, Richard C.
, p. 1626 - 1632 (2007/10/03)
The ICl-induced cyclization of heteroatom-substituted alkynones provides a simple, highly efficient approach to various 3-iodochromones and analogues. This process is run under mild conditions, tolerates various functional groups, and generally provides chromones in good to excellent yields. Subsequent palladium-catalyzed transformations afford a rapid increase in molecular complexity and a convenient preparation of a wide range of functionally substituted chromones, furans, and polycyclic compounds. Iodothiochromenones and iodoquinolinones are also prepared by similar ICl-induced cyclizations.
