890-44-8Relevant academic research and scientific papers
Ruthenium-catalysed C-alkylation of 1,3-dicarbonyl compounds with primary alcohols and synthesis of 3-keto-quinolines
Cini, Elena,Petricci, Elena,Truglio, Giuseppina I.,Vecchio, Marialaura,Taddei, Maurizio
, p. 31386 - 31390 (2016/04/09)
The mono-alkylation of 1,3-diketones using alcohols is possible in the presence of catalytic amounts of Ru(CO)(PPh3)3HCl and 10% mol of the Hantzsch ester. The borrowing hydrogen process between the catalyst and the dihydropyridine/p
Chiral phosphoric acid catalyzed desymmetrization of meso-1,3diones: Asymmetric synthesis of chiral cyclohexenones
Mori, Keiji,Katoh, Takuya,Suzuki, Tohru,Noji, Takuya,Yamanaka, Masahiro,Akiyama, Takahiko
supporting information; experimental part, p. 9652 - 9654 (2010/04/28)
Chiral effectiveness: The title transformation is applicable to a wide variety of substrates to give chiral cyclohexenones in high yields and with excellent enantioselecti vity (see scheme). To clarity the origin of the enantioselectivity ONIOM calculations were carried out
Synthesis of novel indane-1,3-dione derivatives and their biological evaluation as anticoagulant agents
Mitka, Katarzyna,Kowalski, Piotr,Pawelec, Dariusz,Majka, Zbigniew
experimental part, p. 613 - 618 (2010/04/05)
2-Substituted derivatives of indane-1,3-dione 3a-f , 5a-g, 6a-g were synthesized and investigated as anticoagulant agents. 2-Arylindane-1,3-diones (3) were obtained in the reaction of phthalide with appropriate arylaldehydes. 2-Arylmethyleneindane-1,3-diones (5) were prepared by condensation of indane-1,3-dione with the corresponding arylaldehydes. The compounds 5 were converted into their methyl analogues 6 by reduction with sodium tetrahydroborate. All of the compounds studied were screened for the anticoagulant activity. The highest prothrombin time was established for 2-[4-(methylsulfanyl) phenyl]indane-1,3-dione (3c) (PT = 33.71 (± 26.01) s), which was very close to PT of the drug anisindione (PT = 36.0 (± 26.42) s).
Development of pharmaceutical drugs, drug intermediates and ingredients by using direct organo-click reactions
Ramachary, Dhevalapally B.,Kishor, Mamillapalli,Reddy, Y. Vijayendar
supporting information; experimental part, p. 975 - 993 (2009/04/11)
Here we report on our studies of the use of combinations of amino acids, amines, K2CO3 or Cs2CO3 and CuSO4/Cu for catalysing green cascade reactions. We aimed to prepare the highly reactive and substituted olefin species 7 and 8, under very mild and environmentally friendly conditions, thus giving the hydrogenated products 10 and 12 through the action of Hantzsch ester (4) by self-catalysis through decreasing the HOMO-LUMO energy gaps between olefins 7/8 and Hantzsch ester (4) through biomimetic reductions. Highly useful compounds 10 to 14 were assembled from simple substrates such as aldehydes 1, ketones 2, CH acids 3, Hantzsch ester (4) and alkyl halides 5 by diversity-oriented green synthesis involving cascade olefination/hydrogenation (O/H), olefination/hydrogenation/alkylation (O/H/A) and hydrogenation/olefination/hydrogenation (H/O/H) reaction sequences in one-pot fashion with stereospecific organo- and organo-/metal-carbonate catalysis. Highly functionalized diverse compounds such as 10 to 14 are biologically active products and have found wide applications as pharmaceutical drugs, drug intermediates and drug ingredients. For the first time in organocatalysis, we report the O/H/A/TE reaction to furnish high yields of transesterification products 11 by simply mixing the reactants under proline/K2CO3 catalysis conditions. Additionally, a novel organocatalytic H/O/H reaction sequence for the synthesis of alkyl-substituted aromatics has been developed. Furthermore, for the first time we have developed organocatalysed cascade olefination/hydrogenation/hydrolysis (O/H/H) reactions to furnish highly useful materials such as 2-oxochroman-3-carboxylic acid (14kc) and 2-amino-4H-chromene-3-carbonitrile (14kj) in good yields. Experimentally simple and environmentally friendly organocatalytic two-carbon homologation through cascade O/H/H reactions of aldehydes 1, Meldrum's acid (3c), Hantzsch ester (4) and acetic acid/triethylamine in ethanol has been demonstrated. Additionally, we have developed a green synthesis of the highly substituted 1,2,3-triazole 17 from simple substrates through a two-step combination of olefination/hydrogenation/alkylation and Huisgen cycloaddition reaction sequences under stereospecific organocopper catalysis conditions. In this paper we have found strong support for our hypothesis that, "decreasing the HOMO-LUMO energy gap between olefins 7/8 and Hantzsch ester (4) will drive the biomimetic hydrogenation reaction by self-catalysis". This self-catalysis was further confirmed with many varieties of examples. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Towards organo-click reactions: Development of pharmaceutical ingredients by using direct organocatalytic bio-mimetic reductions
Ramachary, Dhevalapally B.,Reddy, G. Babul
, p. 4463 - 4468 (2008/09/19)
Economic and environmentally friendly bio-mimetic one-pot three and four-component Knoevenagel-hydrogenation (K-H), five-component Knoevenagel-hydrogenation-alkylation (K-H-A) and six-component Knoevenagel-hydrogenation-alkylation-Huisgen cycloaddition (K-H-A-HC) reactions of aldehydes, CH-acids, o-phenylenediamine, alkyl halides and azides using proline, proline-metal carbonate and proline-metal carbonate-Cu I-catalysis, respectively have been developed. Many of K-H and K-H-A compounds have direct application in pharmaceutical chemistry. The Royal Society of Chemistry.
A novel and green protocol for two-carbon homologation: A direct amino acid/K2CO3-catalyzed four-component reaction of aldehydes, active methylenes, Hantzsch esters and alkyl halides
Ramachary, Dhevalapally B.,Kishor,Ramakumar
, p. 651 - 656 (2007/10/03)
A novel and green approach for the two-carbon homologation of aldehydes using amino acid catalysis has been developed and further extended to the generation of pharmaceutically active cyano-esters via four-component reactions in one-pot.
Synthesis, structure, and nucleophile-induced rearrangements of spiroketones
Maslak, Przemyslaw,Varadarajan, Sridhar,Burkey, Jeffrey D.
, p. 8201 - 8209 (2007/10/03)
Three tetraketones based on the 2,2'-spirobiindan-1,1',3,3'-tetraone skeleton were prepared and investigated. All three compounds show spiroconjugation between their perpendicular π-networks. The interaction results in lowering of the energy of the LUMO of the systems by ca. 0.2-0.3 eV as compared to non-spiroconjugated models. The spiroketones are susceptible to nucleophile-induced retro-Claisen condensations that lead to molecular rearrangements destroying spiro connectivity.
ACID HYDROLYSIS OF N-METHYL DERIVATIVES OF 4-PHENYL-5-OXO-4,5-DEHYDROINDENOPYRIDINE
Lusis, V. K.,Mutsenietse, D. Kh.,Dubur, G. Ya.
, p. 1104 - 1107 (2007/10/02)
The splitting of the dihydropyridine ring of N-methyl-substituted 4-phenyl-5-oxo-4,5-dihydroindenopyridine in an acid medium takes place at the C-N bond.During the splitting of 1,2-dimethyl-4-phenyl-4,5-dihydroindenopyridine, 4-phenyl-4-(ind
