5292-54-6Relevant academic research and scientific papers
AlCl3 catalyzed coupling of: N-benzylic sulfonamides with 2-substituted cyanoacetates through carbon-nitrogen bond cleavage
Hu, Chen,Hong, Gang,Qian, Xiaofei,Kim, Kwang Rim,Zhu, Xiaoyan,Wang, Limin
, p. 4984 - 4991 (2017/07/10)
A new cross-coupling reaction of N-benzylic sulfonamides with 2-substituted cyanoacetates for the synthesis of 2-substituted benzylbenzene was reported. In the presence of AlCl3, a broad range of N-benzylic sulfonamides reacted smoothly with 2-substituted cyanoacetates to afford structurally diverse benzylbenzenes in moderate to excellent yields. The conversion could be enlarged to gram-scale efficiently. The practicability of this approach was further manifested in the synthesis of a related bioactive agent with high anti-inflammatory activity.
Fe-catalyzed double cross-dehydrogenative coupling of 1,3-dicarbonyl compounds and arylmethanes
Yang, Kai,Song, Qiuling
supporting information, p. 548 - 551 (2015/03/05)
Fe-catalyzed tandem cross-dehydrogenative coupling of the methyl group in arylmethanes with 1,3-dicarbonyl compounds has been developed. The reaction affords one new C(sp3)-C(sp2) bond and one new C(sp3)-C(sp3)
Fe(HSO4)3 : An efficient, heterogeneous and reusable catalyst for C-alkylation of β-dicarbonyl compounds
Khafajeh, Samaneh,Akhlaghinia, Batool,Rezazadeh, Soodabeh,Eshghi, Hossein
, p. 1903 - 1912 (2015/02/05)
Fe(HSO4)3(FHS) was used as an efficient catalyst for the heterogeneous addition of a series of benzylic and allylic alcohols to various β-dicarbonyl compounds, which afforded moderate to excellent yields of C-alkylated products in 1,2-dichloroethane. In comparison with the previous methods, the present research surprisingly exhibited higher reaction yields without formation of any by-products which could be formed by self-condensation of alcohols. Moreover, the catalyst can be readily recovered and reused up to five times with almost maintained reactivity and yields.
Efficient nucleophilic substitution of -aryl alcohols with 1,3-dicarbonyl compounds catalyzed by tin ion-exchanged montmorillonite
Wang, Jiacheng,Masui, Yoichi,Onaka, Makoto
experimental part, p. 2493 - 2497 (2010/12/18)
Tin ion-exchanged montmorillonite demonstrated the high catalytic activity for the direct nucleophilic substitution of a hydroxyl group in -aryl alcohols with various 1,3-dicarbonyl compounds including less acidic 1,3-diesters in crude solvents to afford
Fe(ClO4)3·×H2O-Catalyzed direct C-C bond forming reactions between secondary benzylic alcohols with different types of nucleophiles
Thirupathi, Ponnaboina,Kim, Sung Soo
experimental part, p. 2995 - 3003 (2010/06/14)
Fe(ClO4)3·×H2O as a highly effective catalyst for benzylation of 1,3-dikones, β-ketoesters, 1,3-diesters, electron-rich arenes and heteroarenes and 4-hydroxycoumarin with various benzylic alcohols is described. The usefulness of this procedure is shown by a synthesis of bis-symmetrical triarylmethanes and one step synthesis of an anti-coagulant compound 4-hydroxy-3-(1,2,3,4-tetrahydronaphthalen-1-yl)-2H-chromen-2-one (Coumatetralyl (B)). The advantages of this protocol are broad scope, mild conditions, use of inexpensive catalyst and simplicity of operation since water is the only side product.
Tris(pentafluorophenyl)borane-catalyzed alkylation of 1,3-dicarbonyl compounds with benzylic alcohols: Access to oxygenated heterocycles
Reddy, Chada Raji,Vijaykumar, Jonnalagadda,Gree, Rene
experimental part, p. 3715 - 3723 (2010/12/19)
Tris(pentafluorophenyl)borane has found to be an effective catalyst for the alkylation of 1,3-dicarbonyl compounds using benzylic alcohols as alkylating agents. Various 1,3-dicarbonyl compounds reacted cleanly with different benzylic alcohols to provide t
Microwave-irradiated transition-metal catalysis: Rapid and efficient dehydrative carbon-carbon coupling of alcohols with active methylenes
Babu, Srinivasarao Arulananda,Yasuda, Makoto,Tsukahara, Yasunori,Yamauchi, Tomohisa,Wada, Yuji,Baba, Akio
, p. 1717 - 1724 (2008/12/22)
A rapid and highly productive synthetic microwave-irradiation protocol for transition-metal-catalyzed carbon-carbon coupling of a wide range of benzylic/allylic alcohols with β-diones, β-keto esters, and dialkyl malonates is reported. In a representative
A simple and efficient FeCl3-catalyzed direct alkylation of active methylene compounds with benzylic and allylic alcohols under mild conditions
Jana, Umasish,Biswas, Srijit,Maiti, Sukhendu
, p. 4065 - 4069 (2008/02/03)
A highly efficient FeCl3-catalyzed alkylation of various active methylene compounds with various benzylic or allylic alcohols under mild conditions has been developed. The reaction was carried out in the presence of a catalytic amount of anhydr
4-Amino-5-aryl-6-arylethynylpyrimidines: Structure-activity relationships of non-nucleoside adenosine kinase inhibitors
Matulenko, Mark A.,Paight, Ernest S.,Frey, Robin R.,Gomtsyan, Arthur,DiDomenico Jr., Stanley,Jiang, Meiqun,Lee, Chih-Hung,Stewart, Andrew O.,Yu, Haixia,Kohlhaas, Kathy L.,Alexander, Karen M.,McGaraughty, Steve,Mikusa, Joseph,Marsh, Kennan C.,Muchmore, Steven W.,Jakob, Clarissa L.,Kowaluk, Elizabeth A.,Jarvis, Michael F.,Bhagwat, Shripad S.
, p. 1586 - 1605 (2008/02/01)
A series of non-nucleoside adenosine kinase (AK) inhibitors is reported. These inhibitors originated from the modification of 5-(3-bromophenyl)-7-(6-morpholin-4-ylpyridin-3-yl)pyrido[2,3-d]pyrimidin-4-ylamine (ABT-702). The identification of a linker that would approximate the spatial arrangement found between the pyrimidine ring and the aryl group at C(7) in ABT-702 was a key element in this modification. A search of potential linkers led to the discovery of an acetylene moiety as a suitable scaffold. It was hypothesized that the aryl acetylenes, ABT-702, and adenosine bound to the active site of AK (closed form) in a similar manner with respect to the orientation of the heterocyclic base. Although potent acetylene analogs were discovered based on this assumption, an X-ray crystal structure of 5-(4-dimethylaminophenyl)-6-(6-morpholin-4-ylpyridin-3-ylethynyl)pyrimidin-4-ylamine (16a) revealed a binding orientation contrary to adenosine. In addition, this compound bound tightly to a unique open conformation of AK. The structure-activity relationships and unique ligand orientation and protein conformation are discussed.
Direct carbon-carbon bond formation from alcohols and active methylenes, alkoxyketones, or indoles catalyzed by indium trichloride
Yasuda, Makoto,Somyo, Toshio,Baba, Akio
, p. 793 - 796 (2007/10/03)
(Chemical Equation Presented) The unsalted variety: The direct coupling reaction of alcohols with active methylenes, alkoxyketones, or indoles catalyzed by InCl3 proceeds without the formation of metal salts (see scheme). As H2O is the only by-product of this system, the alkylated products are easily isolated in pure form, and the reaction is suitable for large-scale synthesis.
