40888-66-2Relevant academic research and scientific papers
A facile, efficient and solvent-free titanium (IV) ethoxide catalysed knoevenagel condensation of aldehydes and active methylenes
Ramaiah, Manjunatha M.,Shivananju, Nanjunda Swamy,Shubha, Priya Babu
, p. 107 - 115 (2020/02/04)
Titanium ethoxide has been employed as a novel and efficient reagent for the Knoevenagel condensation of aldehydes with active methylenes such as diethyl malonate and ethyl cyanoacetate under solvent free conditions to afford substituted olefins in high to excellent yields. The reaction is suitable for a variety of aromatic, aliphatic and heteroaromatic aldehydes with various active methylenes. Parallel to this, microwave irradiation has been utilized to achieve improved reaction rates and enhanced yields. Herein, we illustrated a convenient method for the preparation of α,β-unsaturated compounds using both conventional and microwave irradiation methods. An efficient and solvent free Knoevenagel condensation between aldehydes and active methylenes was developed using titanium ethoxide. The procedure proved to be successful with a wide range of substrates such as aromatic, aliphatic and heterocyclic aldehydes and various active methylenes to afford substituted olefins. The reaction was also carried out under microwave irradiation to accomplish the corresponding olefins with improved reaction rates, yields and cleaner reaction profiles.We have developed an efficient and novel methodology for the synthesis of olefinic compounds by Knoevenagel condensation under solvent-free conditions using titanium ethoxide, for the first time, as a reagent as well as a solvent. This method is appropriate for the synthesis of a variety of aromatic aldehydes containing various electron-donating and withdrawing groups, aliphatic and heteroaromatic aldehydes. The significant advantages offered by this methodology could be applied to various active methylenes in order to offer the corresponding Knoevenagel products. Thus, we believe that this method delivers high conversions, cleaner reaction profiles under solvent-free reaction conditions and shorter reaction times, all of which make it a very useful and attractive approach for the preparation of a wide range of substituted olefins.
A Regioselective Approach to C3-Aroylcoumarins via Cobalt-Catalyzed C(sp 2)-H Activation Carbonylation of Coumarins
Ansari, Samira,Mirzaei, Siyavash,Pashazadeh, Rahim,Rajai-Daryasarei, Saideh,Shabanian, Meisam,Soheilizad, Mehdi
supporting information, p. 3014 - 3020 (2019/07/22)
A new cobalt-catalyzed C-H bond activation of coumarins with aryl halides or pseudohalides and carbon monoxide insertion to give various 3-aroylcoumarin derivatives is described. It is the first time that CO as C1 feedstock is used as the coupling partners in cobalt-catalyzed regioselective coumarin C-H functionalization reactions. Upon activation with manganese powder, the Co catalyzes the C-H bond activation carbonylation reactions of aryl iodides, bromides, and even triflates under mild conditions, providing the regioselective aroylated products in moderate to good yields.
A Regioselective Metal-Free Construction of 3-Aroyl Coumarins by Csp2-H Functionalization
Jafarpour, Farnaz,Abbasnia, Masoumeh
, p. 11982 - 11986 (2016/12/09)
A successive metal-free TBHP-mediated regioselective C-H functionalization of coumarins toward expedient synthesis of 3-aroyl coumarins is unveiled. The ongoing method conducted through the reaction of either coumarins or coumarin-3-carboxylic acids with
Regioselective transition metal-free acylation of coumarins via cross-dehydrogenative coupling reaction of coumarins and aldehydes
Adib, Mehdi,Rajai-Daryasarei, Saideh,Pashazadeh, Rahim,Tajik, Mahnaz,Mirzaei, Peiman
, p. 3701 - 3705 (2016/07/26)
A transition metal-free cross-dehydrogenative coupling reaction is described for the preparation of 3-acylcoumarins. Heating a mixture of a coumarin, an aldehyde, and the K2S2O8/Aliquat 336 system in chlorobenzene at 100 °C for 8 h regioselectively afforded the corresponding 3-acylcoumarin derivatives in good to excellent yields.
Regioselective Coupling Reactions of Coumarins with Aldehydes or Di-tert-butyl Peroxide (DTBP) through a C(sp2)-H Functionalization Process
Zhao, Wannian,Xu, Lei,Ding, Yingcai,Niu, Ben,Xie, Ping,Bian, Zhaogang,Zhang, Denghong,Zhou, Aihua
, p. 325 - 330 (2016/02/14)
Coumarin derivatives are highly valuable compounds in drug discovery. Herein, we have developed two new coupling reactions that involve coumarins and either aldehydes or di-tert-butyl peroxide (DTBP) in the presence of inexpensive copper or iron catalysts. Both of these reactions proceed through a C(sp2)-H functionalization process to regioselectivity generate keto- or methyl-substituted coumarin derivatives in moderate to good yields These coupling reactions will enrich current coumarin chemistry.
Diacylation of coumarins by silver-catalyzed decarboxylative cross-coupling
Wang, Hua,Zhou, Shi-Liu,Guo, Li-Na,Duan, Xin-Hua
, p. 630 - 636 (2015/02/02)
A mild silver-catalyzed decarboxylative acylation of coumarins has been developed by using α-oxocarboxylic acids as acyl sources. This protocol provides an efficient and straightforward access to aroyl substituted coumarins in moderate to excellent yields with good selectivities. Furthermore, the reaction conditions were also applicable to quinolinones and naphthoquinones, affording the corresponding acylated heterocyclic compounds.
Iron-catalyzed regioselective direct coupling of aromatic aldehydes with coumarins leading to 3-aroyl coumarins
Yuan, Jin-Wei,Yin, Qiu-Yue,Yang, Liang-Ru,Mai, Wen-Peng,Mao, Pu,Xiao, Yong-Mei,Qu, Ling-Bo
, p. 88258 - 88265 (2015/11/09)
An efficient protocol for iron-catalyzed cross-coupling of coumarins with aromatic aldehydes has been developed. The various 3-aroyl coumarins were selectively afforded in moderate yields. Some notable features of this protocol are high efficiency, wide f
TRI - AND TETRACYCLIC PYRAZOLO[3,4-B]PYRIDINE COMPOUNDS AS ANTINEOPLASTIC AGENT
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Paragraph 0302; 0303; 0304; 0305, (2014/02/16)
The present invention relates to compounds of following general formula (I): and to the pharmaceutically acceptable salts of same, the tautomers of same, the stereoisomers or mixture of stereoisomers in any proportions of same, such as a mixture of enantiomers, notably a racemic mixture, as well as to methods for preparing same and uses of same, notably as an antineoplastic agent.
Synthesis and electrochemical and biological studies of novel coumarin-chalcone hybrid compounds
Pérez-Cruz, Fernanda,Vazquez-Rodriguez, Saleta,Matos, Maria Jo?o,Herrera-Morales, Alejandra,Villamena, Frederick A.,Das, Amlan,Gopalakrishnan, Bhavani,Olea-Azar, Claudio,Santana, Lourdes,Uriarte, Eugenio
, p. 6136 - 6145 (2013/09/02)
A series of novel hydroxy-coumarin-chalcone hybrid compounds 2a-i has been synthesized by employing a simple and efficient methodology. An electrochemical characterization using cyclic voltammetry and ESR spectroscopy were carried out to characterize the
TRI- AND TETRACYCLIC PYRAZOLO[3,4-B]PYRIDINE COMPOUNDS AS ANTINEOPLASTIC AGENT
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Page/Page column 58, (2012/11/06)
The present invention relates to compounds of following general formula (I): and to the pharmaceutically acceptable salts of same, the tautomers of same, the stereoisomers or mixture of stereoisomers in any proportions of same, such as a mixture of enantiomers, notably a racemic mixture, as well as to methods for preparing same and uses of same, notably as an antineoplastic agent
