52159-66-7Relevant academic research and scientific papers
Synthesis of 2-Hydroxy-1-naphthoic Acid Derivatives by Oxidative Cyclization of Esters of 5-Aryl-3-oxopentanoic Acid by Mn(III) and Ce(IV) Salts
Citterio, Attilio,Pesce, Luca,Sebastiano, Roberto,Santi, Roberto
, p. 142 - 144 (1990)
A new synthesis of substituted 2-hydroxy-1-naphthoic acid esters and amides 4 by oxidation of 5-aryl-3-oxopentanoic acid esters or amides 1 with manganese(III) acetate or cerium(IV) ammonium nitrate has been developed, based on the intramolecular homolytic substitution by α-dicarbonylalkyl radicals generated from high-valent metal β-dicarbonyl complexes.
Overcoming the Deallylation Problem: Palladium(II)-Catalyzed Chemo-, Regio-, and Stereoselective Allylic Oxidation of Aryl Allyl Ether, Amine, and Amino Acids
Begam, Hasina Mamataj,Jana, Ranjan,Manna, Kartic,Samanta, Krishanu
supporting information, p. 7443 - 7449 (2020/10/09)
We report herein a Pd(II)/bis-sulfoxide-catalyzed intramolecular allylic C-H acetoxylation of aryl allyl ether, amine, and amino acids with the retention of a labile allyl moiety. Mechanistically, the reaction proceeds through a distinct double-bond isomerization from the allylic to the vinylic position followed by intramolecular carboxypalladation and the β-hydride elimination pathway. For the first time, C-H oxidation of N-allyl-protected amino acids to furnish five-membered heterocycles through 1,3-syn-addition is established with excellent diastereoselectivity.
Ruthenium(II)-catalyzed synthesis of hydroxylated arenes with ester as an effective directing group
Yang, Yiqing,Lin, Yun,Rao, Yu
supporting information; experimental part, p. 2874 - 2877 (2012/07/28)
An unprecedented Ru(II) catalyzed ortho-hydroxylation has been developed for the facile synthesis of a variety of multifunctionalized arenes from easily accessible ethyl benzoates with ester as an efficient directing group. Both the TFA/TFAA cosolvent system and oxidants serve as the critical success factors in this transformation. The reaction demonstrates excellent reactivity, good functional group tolerance, and high yields.
Direct synthesis of esters and amides from unprotected hydroxyaromatic and -aliphatic carboxylic acids
Katritzky, Alan R.,Singh, Sanjay K.,Cai, Chunming,Bobrov, Sergey
, p. 3364 - 3374 (2007/10/03)
A facile method for the activation of hydroxy-substituted carboxylic acids using benzotriazole chemistry without prior protection of the hydroxy substituents is presented. The N-acylbenzotriazole intermediates 2a-g, 6a-d, and 9a-c have been used for high-yielding synthesis of both aliphatic (3a-1) and aromatic (7a-h, 10a-f) hydroxy carboxamides. High yields of aromatic hydroxy esters 12a-h and 13a-i were obtained using either neat alcohols in neutral microwave conditions or nucleophilic alkoxides and the intermediate N-(arylacyl)benzotriazoles. Moderate yields were obtained in the case of aliphatic hydroxy esters 11a,b and thiolesters 11e-g from the intermediates 2a-c.
A new method for the synthesis of 2-cyclopenten-1-one-5-carboxylic ester derivatives via Rh2(OAc)4-mediated intramolecular C-H insertion reaction of 4Z-β-vinyl-α-diazo β-ketoesters
Deng, Guisheng,Xu, Baihua,Wang, Jianbo
, p. 10811 - 10817 (2007/10/03)
2-Cyclopenten-1-one-5-carboxylic ester derivatives 14 are synthesized in a four-step-reaction sequence starting from alkynyl aldehydes 9 via 4Z-β-vinyl-α-diazo β-ketoesters intermediate 8. The synthetic method for 8 is described. When the δ substituent is
