99865-12-0Relevant academic research and scientific papers
A mild and convenient one-pot photochemical synthesis of chroman-4-one derivatives. the photo-Fries rearrangement of (hetero)aryl 3-methyl-2-butenoate esters under basic catalysis
López, Cecilia Samaniego,Erra-Balsells, Rosa,Bonesi, Sergio M.
, p. 4387 - 4390 (2010)
The biphasic base catalysis-mediated photo-Fries rearrangement reaction of aryl 3-methy-2-butenoate esters in room temperature cyclohexane - 10% KOH system was investigated. This mild photochemical reaction leads to the formation of chroman-4-one derivatives in good to high yield and in short reaction times (30-120 min) in a one-pot photochemical reaction. Also, the photochemical reaction, as a convenient, versatile, and general method, applies efficiently to polycyclic and heterocyclic 3-methy-2-butenaote esters.
5-Aryl indanones and derivatives as non-steroidal progesterone receptor modulators
Kern, Jeffrey C.,Terefenko, Eugene,Trybulski, Eugene,Berrodin, Thomas J.,Cohen, Jeffrey,Winneker, Richard C.,Yudt, Matthew R.,Zhang, Zhiming,Zhu, Yuan,Zhang, Puwen
, p. 6666 - 6669 (2009)
Novel 5-aryl indanones, inden-1-one oximes, and inden-1-ols were synthesized and evaluated as progesterone receptor (PR) modulators using the T47D cell alkaline phosphatase assay. Both PR agonists and antagonists were achieved with appropriate 3- and 5-su
Formation of 2,2-dimethylchroman-4-ones during the photoinduced rearrangement of some aryl 3-methyl-2-butenoate esters. A mechanistic insight
Iguchi, Daniela,Erra-Balsells, Rosa,Bonesi, Sergio M.
, p. 1903 - 1910 (2016/04/05)
Several aryl 3-methyl-2-butenoate esters upon irradiation lead to the formation of [1,3]-migrated photoproducts, phenol and, surprisingly 2,2-dimethylchroman-4-one derivatives. The starting photochemical reaction takes place from the singlet excited state of the ester and as a total mechanism two consecutive reaction pathways are proposed. The former involves the photo-Fries rearrangement of the esters in all the solvents studied and, depending on the proticity of the solvent, the latter involves an ESIPT process followed by thermal 6π-electrocyclic reaction and/or thermal (intramolecular oxa-Michael addition) cyclization of the ortho regioisomers photoformed. This second pathway is responsible of the formation of the 2,2-dimethylchroman-4-one derivatives.
ON THE REACTION OF SUBSTITUTED PHENOLS AND 3-METHYLBUT-2-ENOIC ACID. A COMPARATIVE STUDY
Seboek, Peter,Jekoe, Jozsef,Timar, Tibor,Jaszberenyi, Joseph Cs.
, p. 2099 - 2114 (2007/10/02)
A systematic and comparative study of the reaction of a series of substituted phenols and 3-methylbut-2-enoic acid in zinc chloride/phosphorus oxychloride and aluminum chloride/phosphorus oxychloride reveals that the formation of phenolic esters and 2,2-dimethyl-4-chromanones is strongly influenced by the substituents, their popsition on the aromatic ring of the starting phenols.Based on our study, a mixed Friedel-Crafts and Fries rearrangement mechanism is in operation in these reactions.
On the synthesis of substituted 2,2-dimethyl1-4-chromanones and related compounds
Seboek, Peter,Jekoe, Jozsef,Timar, Tibor,Jaszberenyi, Joseph Cs.
, p. 2791 - 2794 (2007/10/02)
A systematic study of the reaction of a series of monosubstituted phenols 3 and 3-methylbut-2-enoic acid 4 in phosphorus oxychloride/zinc chloride revealed that the formation of 4-chromanones was strongly infuenced by the substituents and their position on the aromatic ring of the starting phenols.
