- Stereoselective synthesis of (Z)-3-ylidenephthalides via AlCl3-mediated cyclization with 2-acylbenzoic acids
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An efficient method for the synthesis of (Z)-3-ylidenephthalides is reported in moderate to high yield with AlCl3 as catalyst. Different substrates of the 2-acylbenzoic acids are well performed in the Z/E selectivity. This method is highlighted
- Feng, Ziming,Jiang, Jianshuang,Li, Gangsheng,Wang, Xujie,Yang, Yanan,Zhang, Peicheng,Zhang, Xu
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- A palladium iodide catalyzed regioselective carbonylative route to isocoumarin and thienopyranone carboxylic esters
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The reactivity of 2-alkynylbenzoic acids under PdI2/KI-catalyzed oxidative alkoxycarbonylation conditions, with oxygen (from air) as external oxidant and an alcohol as external nucleophile, has been studied. It was found that substrates with triple bond substituted with a bulky alkyl group, such as tert-butyl, selectively underwent a 6-endo-dig cyclization - alkoxycarbonylation pathway with ethanol or isopropanol as nucleophile, to give high value added isocoumarin-4-carboxylic esters in good to high yields (67–87%). When applied to alkynylthiophencarboxylic acids bearing an internal triple bond, the reaction turned out to be completely regioselective toward the formation of the corresponding alkyl thienopyranonecarboxylates ensuing from 6-endo-dig cyclization-alkoxycarbonylation, regardless the nature of the substituent on the triple bond and the external alcohol (54–91% yields). To confirm the structure of the products deriving from different kinds of substrates, and therefore to corroborate the proposed mechanistic pathways, the crystalline structures of 11 new compounds have been resolved by XRD analysis.
- Carfagna, Carla,Centore, Roberto,Cuocci, Corrado,Della Ca', Nicola,Gabriele, Bartolo,Mancuso, Raffaella,Novello, Mariangela,Olivieri, Diego,Ziccarelli, Ida
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p. 164 - 182
(2021/12/20)
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- Use of Imidazo[1,5-a]pyridin-3-ylidene as a Platform for Metal-Imidazole Cooperative Catalysis: Silver-Catalyzed Cyclization of Alkyne-Tethered Carboxylic Acids
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Silver complexes with 5-(4-(tert-butyl)-1H-imidazol-1-yl)-imidazo[1,5-a]pyridin-3-ylidene ligands were synthesized as metal-imidazole acid-base cooperative catalysts. Single crystal XRD analysis revealed that the silver atom was located in the vicinity of
- Rawat, Vishal Kumar,Higashida, Kosuke,Sawamura, Masaya
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p. 1631 - 1637
(2021/02/03)
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- Stereoselective synthesis method of (Z)-3-alkenyl phthalide derivative
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The invention discloses a stereoselective synthesis method of a (Z)-3-alkenyl phthalide derivative, which comprises the specific steps of stereoselectively synthesizing the (Z)-3-alkenyl phthalide derivative from a 2-acyl benzoic acid compound under the catalytic action of aluminum trichloride, dissolving the 2-acyl benzoic acid compound shown in a formula (I) defined in the description as a raw material in an organic solvent, and stereoselectively preparing a compound as shown in a formula (II) defined in the description by taking Al as a catalyst. According to the synthesis method of the (Z)-3-alkenyl phthalide derivative, the used catalyst is cheap and easy to obtain, the reaction condition is mild, the product is easy to purify, the stereoselectivity is good, the yield is high, the synthesis method is suitable for industrial production, and a new method is provided for preparing the (Z)-3-alkenyl phthalide derivative.
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Paragraph 0021; 0083-0087
(2021/06/23)
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- Iridium-Catalyzed Cycloisomerization of Alkynoic Acids: Synthesis of Unsaturated Lactones
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The iridium-catalyzed cycloisomerization of various alkynoic acids was successfully developed, and a series of five-, six-, and especially seven-membered unsaturated lactones were constructed with moderate yields and excellent regioselectivities (up to 68
- Huang, Yi,Zhang, Xianghe,Dong, Xiu-Qin,Zhang, Xumu
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p. 782 - 788
(2020/01/08)
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- Palladium/Copper-Catalyzed Denitrogenative Alkylidenation and ortho-Alkynylation Reaction of 1,2,3-Benzotriazin-4(3 H)-ones
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An efficient palladium-catalyzed approach to access various functionalized (Z)-3-benzylidene-isoindoline-1-ones and (Z)-3-benzylidene(imino)isobenzofuranones via a denitrogenative tandem alkynylation/cyclization reaction of 1,2,3-benzotriazin-4(3H)-ones w
- Hari Balakrishnan, Madasamy,Mannathan, Subramaniyan
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supporting information
p. 542 - 546
(2020/02/04)
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- Imidazo[2,1-a]isoindole scaffold as an uncharted structure active on Leishmania donovani
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The human protozoan parasites Leishmania donovani and L. infantum are the causative agents of visceral leishmaniasis, as such, responsible for approximately 30,000 deaths annually. The available chemotherapeutic treatments are reduced to a few drugs whose effectiveness is limited by rising drug resistance/therapeutic failure, and noxious side-effects. Therefore, new therapeutic hits are needed. Compounds displaying the imidazo[2,1-a]isoindole skeleton have shown antichagasic, anti-HIV, antimalarial and anorectic activities. Here, we report the leishmanicidal activity of thirty one imidazo[2,1-a]isoindol-5-ol derivatives on promastigotes and intracellular amastigotes of L. donovani. Eight out of thirty one assayed compounds showed EC50 values ranging between 1 and 2 μM with selectivity indexes from 29 to 69 on infected THP-1 cells. Six compounds were selected for further elucidation of their leishmanicidal mechanism. In this regard, compound 29, the imidazoisoindolol with the highest activity on intracellular amastigotes, induced an early decrease of intracellular ATP levels, as well as mitochondrial depolarization, together with a partial plasma membrane destructuration, as assessed by transmission electron microscopy. Consequently, the inhibition of the energy metabolism of Leishmania plays an important role in the leishmanicidal mechanism of this compound, even when other additional targets cannot be ruled out. In all, the results supported the inclusion of the imidazoisoindole scaffold for the development of new leishmanicidal drugs.
- Arsène, Sobinson,Gómez-Pérez, Verónica,Escarcena, Ricardo,Abengózar, María ángeles,García-Hernández, Raquel,Nácher-Vázquez, Montserrat,San Feliciano, Arturo,Gamarro, Francisco,Rivas, Luis,Olmo, Esther del
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- Ag2O nanoparticle-catalyzed substrate-controlled regioselectivities: direct access to 3-ylidenephthalides and isocoumarins
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Herein, we disclose the first example of an efficient, silver oxide nanoparticle-catalyzed, direct regioselective synthesis of 3-ylidenephthalides 11-16 and isocoumarins 17-20via sonogashira type coupling followed by substrate-controlled 5-exo-dig or 6-endo-dig cyclization reaction, respectively. This one pot coupling involves reaction of substituted 2-halobenzoic acid with meta/para-substituted and ortho-substituted terminal alkynes, which proceeded in a regioselective manner resulting in the formation of 3-ylidenephthalides or isocoumarins, respectively, in excellent yields (up to 95%) with complete Z-selectivity. This protocol features relatively broad substrate scope, mild conditions, operational simplicity, and is favourable with aromatic/alicyclic terminal alkynes. The competition experiments and gram-scale synthesis further highlight the importance and versatility of the methodology. The proposed mechanistic pathways illustrate that the regioselectivity is substantially being controlled by the substituent(s) present on the acetylenic phenyl ring.
- Chaudhary, Sandeep,Shyamlal, Bharti Rajesh K.,Yadav, Lalit,Tiwari, Mohit K.,Kumar, Krishan
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p. 23152 - 23162
(2018/07/10)
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- Divergent Syntheses of (Z)-3-Alkylideneisobenzofuran-1(3 H)-ones and 1 H-Isochromen-1-ones by Copper-Catalyzed Cycloisomerization of 2-Alkynylbenzoic Acids in Ionic Liquids
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The cycloisomerization of readily available 2-alkynylbenzoic acids 1 in ionic liquids (ILs) as recyclable reaction media has been studied under the catalytic action of CuCl2. With substrates bearing an aryl group on the triple bond, a mixture o
- Mancuso, Raffaella,Pomelli, Christian S.,Chiappetta, Piera,Gioia, Katia F.,Maner, Asif,Marino, Nadia,Veltri, Lucia,Chiappe, Cinzia,Gabriele, Bartolo
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p. 6673 - 6680
(2018/06/01)
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- A highly active diradical cobalt(iii) catalyst for the cycloisomerization of alkynoic acids
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The first cobalt-catalysed cycloisomerisation of alkynoic acids is reported, thanks to the design of a well-defined diradical cobalt(iii) catalyst, in the absence of any additives. The high efficiency, regioselectivity and chemoselectivity are comparable to those of noble metal-based systems. The unique reactivity might be attributed to second coordination sphere effects.
- Leconte, Nicolas,Du Moulinet D'Hardemare, Amaury,Philouze, Christian,Thomas, Fabrice
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supporting information
p. 8241 - 8244
(2018/07/29)
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- 1-Phenyl-1,2-benziodoxol-3-(1H)-one as Synthon for Phthalide Synthesis through Pd-Free, Base-Free, Sonogashira-Type Coupling Cyclization Reaction
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Hypervalent iodine(III) five-membered heterocycles have found broad application as atom-transfer reagents for organic synthesis. Among them, 1-phenyl-1,2-benziodoxol-3-(1H)-one is known as a traditional benzyne precursor, but no further synthetic applicat
- Almasalma, Ahmad A.,Mejía, Esteban
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p. 188 - 195
(2017/11/30)
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- Palladium-catalyzed carbonylative synthesis of isocoumarins and phthalides by using phenyl formate as a carbon monoxide source
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A simple and efficient palladium-catalyzed intramolecular carbonylative synthesis of isocoumarins and phthalides from the easily available starting materials by employing phenyl formate as a CO surrogate has been achieved. The approach affords target compounds in good to excellent yields with the advantages of lower toxicity, milder conditions, easy operation and wide functional group tolerance.
- Yuan, Qing,Chen, Zhen-Bang,Zhang, Fang-Ling,Zhu, Yong-Ming
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p. 1628 - 1635
(2017/02/23)
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- A comparative synthesis of 6-benzyl-2,3-dihydroimidazo[2,1-a]phthalazine and 2H-7-benzyl-3,4-dihydropyrimido[2,1-a]phthalazine
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Two new synthetic strategies have been developed for the synthesis of a new class of cyclophthalazine derivatives. 6-Benzyl-2,3-dihydroimidazo[2,1-a]phthalazine and 2H-7-benzyl-3,4-dihydropyrimido[2,1-a]phthalazine were obtained (i) by intramolecular cyclization of the 2-(aminoalkyl)-4-benzyl-2H-phthalazin-1-one or (ii) by intramolecular cyclization of the corresponding 2-(4-benzylphthalazin-1(2H)-ylideneamino)alcohols previously prepared. The second of the described routes afforded the desired derivatives in high yields.
- Munín, Javier,Santana, Lourdes,Uriarte, Eugenio,Borges, Fernanda,Quezada, Elías
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p. 828 - 830
(2015/03/03)
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- Copper-catalyzed selective synthesis of isoindolin-1-ones and isoquinolin-1-ones from the three-component coupling of 2-halobenzoic acid, alkynylcarboxylic acid and ammonium acetate
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Isoindolin-1-ones and isoquinolin-1-ones were selectively synthesized from the reaction of 2-halobenzoic acid, arylalkynylcarboxylic acid and ammonium acetate (NH4OAc) in the presence of cesium carbonate (Cs2CO3) and a copper catalyst. Conducting the reaction under one-pot conditions provided isoindolin-1-ones in good yields. Changing the addition sequence of ammonium acetate after all reagents had reacted at 120 °C for 6 h selectively produced isoquinolin-1-ones. A variety of arylalkynylcarboxylic acids produced the corresponding isoindolin-1-ones and isoquinolin-1-ones in good yields.
- Irudayanathan, Francis Mariaraj,Noh, Jieun,Choi, Jinseop,Lee, Sunwoo
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p. 3433 - 3442
(2015/01/09)
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- Transition-metal-free synthesis of (Z)-3-ylidenephthalides from 2-acyl-benzoic acids
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We report a highly efficient method for the synthesis of (Z)-3-ylidenephthalides via intramolecular cyclization of readily available 2-acyl-benzoic acids mediated by TSTU at room temperature. Using this method, diversely substituted (Z)-3-ylidenephthalides have been generated in good to excellent yields. The application of the method is highlighted by gram-scale preparation of the antiplatelet drug n-butylphthalide.
- He, Xinhua,Xue, Fengtian
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p. 1956 - 1958
(2014/03/21)
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- Regioselective one-pot synthesis of isocoumarins and phthalides from 2-iodobenzoic acids and alkynes by temperature control
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Copper-catalyzed coupling reaction of 2-iodobenzoic acids and alkynes such as terminal acetylenes, alkynyl carboxylic acids, and trimethylsilylacetylene selectively afforded isocoumarins and phthalides in the presence of cesium carbonate (Cs2CO3) and dimethyl sulfoxide (DMSO). Among the regioselective products, only the 6-endo-dig product, isocoumarin, was formed at 100 °C, and the 5-exo-dig product, phthalide, was formed as a major product at 25 °C. A variety of alkynes produced the corresponding isocoumarins and phthalides in good yields. A mechanism is suggested in which the formation of 2-alkynylbenzoic acid as an intermediate via Sonogashira-type coupling was ruled out in the reaction pathway. Copyright
- Kumar, Manian Rajesh,Irudayanathan, Francis Mariaraj,Moon, Joong Ho,Lee, Sunwoo
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p. 3221 - 3230
(2013/12/04)
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- New method for the synthesis of lactones via nickel-catalyzed isocyanides insertion
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A novel nickel catalyst for the reaction of tert-butyl isocyanide insertion was discovered. In this approach, 1,2-bis(diphenylphosphino)ethane (L3) serves as an efficient ligand, thereby allowing the preparation of lactones from (o-bromophenyl)phenylethanone derivatives. It is noteworthy that this is the first example of nickel acting as a metal catalyst in the reactions of tert-butyl isocyanide insertion. The significance of this methodology may draw many chemists attention in the field of isocyanide-incorporating reactions. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]
- Fei, Xiang-Dong,Tang, Ting,Ge, Zhi-Yuan,Zhu, Yong-Ming
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p. 3262 - 3271
(2013/10/01)
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- 3-Ylidenephthalides as a new class of transient receptor potential channel TRPA1 and TRPM8 modulators
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Following the recent identification of the naturally occurring 3-ylidene-4,5-dihydrophthalide ligustilide and its oxidation product dehydroligustilide as novel TRPA1 modulators, a series of seventeen 3-ylidenephthalides was synthesized and tested on TRPA1 and TRPM8 channels. Most of these compounds acted as strong modulators of the two channel types with EC50 and/or IC50 values distinctly lower than those of the reference compounds.
- Ortar, Giorgio,Schiano Moriello, Aniello,Morera, Enrico,Nalli, Marianna,Di Marzo, Vincenzo,De Petrocellis, Luciano
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p. 5614 - 5618
(2013/10/01)
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- Palladium-catalyzed synthesis of isocoumarins and phthalides via tert -butyl isocyanide insertion
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A novel and highly efficient strategy for the synthesis of isocoumarins and phthalides through a palladium(0)-catalyzed reaction incorporating tert-butyl isocyanide has been developed. This process, providing one of the simplest methods for the synthesis of this class of valuable lactones, involves two steps including cyclization reaction and simple acid hydrolysis. The methodology is tolerant of a wide range of substrates and applicable to library synthesis.
- Fei, Xiang-Dong,Ge, Zhi-Yuan,Tang, Ting,Zhu, Yong-Ming,Ji, Shun-Jun
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p. 10321 - 10328
(2013/01/15)
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- NHC-catalyzed oxidative cyclization reactions of 2-alkynylbenzaldehydes under aerobic conditions: Synthesis of O-Heterocycles
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Chemical equations presented. An NHC-catalyzed, regio- and stereoselective oxidative cyclization of o-alkynylbenzaldehydes bearing an unactivated alkyne moiety as an internal electrophile has been developed to afford phthalides and isocoumarins. A single organocatalytic system enabled two sequential C-O bond formations to take place in an atom economical manner via highly efficient dual activation. Molecular oxygen in air could be utilized as a source of an oxygen atom for the oxidation of aldehydes to the corresponding benzoic acids under our newly developed reagent system.
- Park, Jong Hyub,Bhilare, Sachin V.,Youn, So Won
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p. 2228 - 2231
(2011/07/09)
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- Antimalarial activity of imidazo[2,1-a]isoindol-5-ol derivatives and related compounds
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The synthesis of several series of imidazo[2,1-a]isoindol-5-ol derivatives and the results of their evaluation against Plasmodium falciparum are presented and discussed. The effects of electron-withdrawing or-donating substituents on different parts of the molecule, as well as those produced by the incorporation of an additional fused ring, were analyzed. Several compounds showed significant antimalarial activity in vitro with IC50 values as low as 60 nM and a certain efficacy in vivo by reducing parasitemia in Plasmodium berghei mouse models.
- Olmo, Esther Del,Barboza, Bianca,Chiaradia, Louise D.,Moreno, Alicia,Carrero-Lérida, Juana,González-Pacanowska, Dolores,Mu?oz, Victoria,López-Pérez, José L.,Giménez, Alberto,Benito, Agustín,Martínez, Antonio R.,Ruiz-Pérez, Luis M.,San Feliciano, Arturo
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experimental part
p. 5379 - 5386
(2011/12/14)
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- Copper-catalyzed preparation of γ-alkylidenebutenolides and isocoumarins under mild palladium-free conditions
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A general and efficient copper(I)-catalyzed cross-coupling and heterocyclization reaction of terminal alkynes and β-iodo-α,β- unsaturated acid derivatives has been developed under very mild conditions. This method provides easy access from good to excellent yields of a variety of 5-ylidenebutenolides and 3-substituted isocoumarins with excellent regio- and stereoselectivity. This procedure does not require the use of any expensive supplementary additives, and is palladium-free.
- Inack-Ngi, Samuel,Rahmani, Raphael,Commeiras, Laurent,Chouraqui, Gaelle,Thibonnet, Jerome,Duchene, Alain,Abarbri, Mohamed,Parrain, Jean-Luc
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supporting information; experimental part
p. 779 - 788
(2009/11/30)
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- Synthesis of phthalides via Pd/CNTs-catalyzed reaction of terminal alkynes and o-iodobenzoic acid under copper- and ligand-free conditions
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A phosphine- and copper-free protocol for the synthesis of phthalides via Pd/CNTs-catalyzed tandem coupling-cyclization process has been developed. The palladium immobilized on CNTs showed high catalytic activity, and the reactions with a variety of termi
- Zhou, Lei,Jiang, Huan-Feng
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p. 8449 - 8452
(2008/03/13)
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- Cycloisomerization of γ- and δ-acetylenic acids catalyzed by gold(I) chloride
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We have developed a gold(I)-catalyzed intramolecular cyclization of γ- and δ-alkyne acids in mild conditions yielding various alkylidene lactones. Whereas a slight electronic effect of the R group was observed on the regioselectivity, bulky substituents o
- Marchal, Estelle,Uriac, Philippe,Legouin, Béatrice,Toupet, Lo?c,Weghe, Pierre van de
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p. 9979 - 9990
(2008/02/13)
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- Regioselective synthesis of (E)-5-(tributylstannylmethylidene)-5H-furan-2- ones and (E)-3-(tributylstannylmethylidene)-3H-isobenzofuran-1-ones: Easy access to γ-alkylidenebutenolide and phthalide skeletons
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Regio- and stereoselective synthesis of γ-alkylidene-butenolides and γ-alkylidenephthalides has been achieved through the palladium-catalysed tandem cross-coupling/cyclisation reactions of tributylstannyl-3-iodopropenoate or the 2-iodo benzoate derivatives with tributyltinacetylene. Iododestannylation occurred with inversion of the configuration of the exocyclic double bond in the case of butenolides, but with retention of configuration for the phthalide. The selectivity observed in the Stille reaction was found to be dependent on the nature of the vinyl or the aryl halide. Georg Thieme Verlag Stuttgart.
- Duchene, Alain,Thibonnet, Jerome,Parrain, Jean-Luc,Anselmi, Elsa,Abarbri, Mohamed
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p. 597 - 607
(2007/12/25)
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- Theoretical studies of 5-exo selective intramolecular cyclization of o-alkynylbenzoic acid catalyzed by organic base
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Theoretical studies of the organic base-catalyzed 5-exo intramolecular cyclization of o-alkynylbenzoic acid were documented. The acidic fragment participating in the transition states was shown to reduce the activation energy significantly on the basis of
- Terada, Masahiro,Kanazawa, Chikashi,Yamanaka, Masahiro
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p. 819 - 825
(2008/09/18)
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- Organic-base-catalyzed synthesis of phthalides via highly regioselective intramolecular cyclization reaction
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The organic-base-catalyzed 5-exo intramolecular cyclization reaction of o-alkynylbenzoic acid produces the corresponding phthalide regioselectively in good to excellent yields. The method provides a practical access to the phthalides, an important class o
- Kanazawa, Chikashi,Terada, Masahiro
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p. 933 - 935
(2008/02/04)
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- Regiocontrolled intramolecular cyclizations of carboxylic acids to carbon-carbon triple bonds promoted by acid or base catalyst
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We systematically investigated, for the first time, the relationship between regioselectivity and acid/base effects in the cyclization reactions between carboxylic acids and carbon-carbon triple bonds. We found novel acid- and base-promoted cyclizations to selectively give isocoumarin or pyran-2(2H)-one and phthalide or furan-2(5H)-one skeletons, respectively, and established a catalytic version of regioselective heterocyclic ring synthesis. Density functional theory calculations and application to a short route to thunberginol A were also described.
- Uchiyama, Masanobu,Ozawa, Hiroki,Takuma, Kazuya,Matsumoto, Yotaro,Yonehara, Mitsuhiro,Hiroya, Kou,Sakamoto, Takao
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p. 5517 - 5520
(2007/10/03)
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- Anti-HIV activity of stilbene-related heterocyclic compounds
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Viral transcription has not been routinely targeted in the development of new antiviral drugs. This crucial step of the viral cycle depends on the concerted action of cellular and viral proteins such as NF-κB and Tat. In the present study, stilbene-related heterocyclic compounds including benzalphthalide, phthalazinone, imidazoindole and pyrimidoisoindole derivatives are tested for their anti-HIV activity. Original assays based on recombinant viruses were used to evaluate HIV replication inhibition and stably transfected cell lines were used to evaluate inhibition of Tat and NF-κB proteins. Some of the stilbene-related heterocyclic compounds analysed displayed anti-HIV activity through interference with NF-κB and Tat function. Moreover, compounds inhibiting both targets displayed a stronger activity on viral replication.
- Bedoya, Luis M.,del Olmo, Esther,Sancho, Rocio,Barboza, Bianca,Beltran, Manuela,Garcia-Cadenas, Ana E.,Sanchez-Palomino, Sonsoles,Lopez-Perez, Jose L.,Munoz, Eduardo,Feliciano, Arturo San,Alcami, Jose
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p. 4075 - 4079
(2007/10/03)
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- Vasorelaxant activity of phthalazinones and related compounds
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Several series of dihydrostilbenamide, imidazo[2,1-a]isoindole, pyrimido[2,1-a]isoindole and phthalazinone derivatives were obtained and their vasorelaxant activity was measured on isolated rat aorta rings pre-contracted with phenylephrine (10-5 M). Some phthalazinones attained, practically, the total relaxation of the organ at micromolar concentrations. For the most potent compound 9h (EC50 = 0.43 μM) the affinities for α1A, α1B and α1D adrenergic sub-receptors were determined.
- Olmo, Esther del,Barboza, Bianca,Ybarra, Ma Ines,Lopez-Perez, Jose Luis,Carron, Rosalia,Sevilla, Ma Angeles,Boselli, Cinthia,Feliciano, Arturo San
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p. 2786 - 2790
(2007/10/03)
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- Leishmanicidal activity of some stilbenoids and related heterocyclic compounds
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We have evaluated the leishmanicidal activity of some natural and semisynthetic dihydrostilbenoids and several compounds of other series of dihydrostilbamides, isoindoles, phthalazinones, imidazoisoindoles and pyrimidoisoindoles. The evaluation was performed in vitro, on cultures of cutaneous, mucocutaneous and visceral strains of Leishmania spp. The most potent and selective compounds of these series were the dihydrostilbene piperidides.
- Del Olmo, Esther,Armas, Marlon Garcia,Lopez-Perez, Jose Luis,Muoz, Victoria,Deharo, Eric,San Feliciano, Arturo
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p. 2123 - 2126
(2007/10/03)
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- Structure-activity relationships in a series of bisquaternary bisphthalimidine derivatives modulating the muscarinic M2-receptor allosterically
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Hexane-bisammonium-type compounds containing lateral phthalimide moieties are well-established ligands of the common allosteric binding site of muscarinic M2 receptors. Previous structure-activity relationships (SAR) revealed two positively charged centers and two lateral phthalimide moieties in a defined arrangement to be essential of a high allosteric potency. The purpose of this study was to replace one carbonyl group of the phthalimides with hydrogens, hydroxy, alkoxy, phenyl, benzyl, and benzylidene groups in order to check the influence of these substituents on the allosteric activity in antagonist-linked receptors. The analysis of the quantitative SAR indicated that a high allosteric potency is related to a certain amount of rigidity as well as polarizibility and the ability to form hydrophobic interactions.
- Botero Cid, Hector M.,Tr?nkle, Christian,Baumann, Knut,Pick, Rainer,Mies-Klomfass, Elisabeth,Kostenis, Evi,Mohr, Klaus,Holzgrabe, Ulrike
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p. 2155 - 2164
(2007/10/03)
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- Palladium-catalyzed intramolecular cyclization of o-ethynylbenzoic acids and o-ethynylbenzamides: Preparation of isocoumarins and isoquinolin-1-ones
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Treatment of the o-ethynylbenzoic acids 1A with a catalytic amount of Pd(II) and triethylamine resulted in the 6-endo-dig cyclization to give the 3-substituted isocoumarins 3 as major products in moderate to good yields. Similarly, the palladium-catalyzed
- Sashida,Kawamukai
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p. 1145 - 1148
(2007/10/03)
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- Synthesis of naturally occurring (Z)-3-benzylidenephthalide and (+/-) 3-benzylphthalides
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A convenient method, involving generation of phthalide anion, is described for the synthesis of naturally occurring (Z) 3-benzylidenephthalide (5) and (+/-) 3-benzyl phthalides (6c, 10a-c), starting from phthalides (7a-b).
- Mali, Raghao S.,Massey, Archna P.,Talele, M. I.
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p. 472 - 490
(2007/10/03)
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- Palladium-catalysed heteroannulation with terminal alkynes: Synthesis of phthalides
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The palladium-copper-catalysed heteroannulation of o-iodobenzoic acid 3 with terminal alkynes 4-18 leads to the synthesis of (Z)-3-alkylidenephthalides 19-33 as the major products. In certain cases, the formation of isocoumarins 34-37 is also observed.
- Kundu, Nitya G.,Pal, Manojit,Nandi, Bidisha
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p. 561 - 568
(2007/10/03)
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- Microwaves assisted Gabriel synthesis of phthalides
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Cesium acetate was found to be the best catalyst for the synthesis of 3-benzylidephthalide from phthalic anhydride and phenylacetic acid. Reasonable to good yields of different 3-arylmethylenephthalides were isolated from the microwave. Gabriel synthesis, even when phenylthio- and 2-(3-)thienyl- acetic acids were used as the starting material.
- Lacova, Margita,Chovancova, Jarmila,Veverkova, Eva,Toma, Stefan
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p. 14995 - 15006
(2007/10/03)
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- SILVER CATALYZED CYCLIZATION OF ALKYNOIC ACIDS: EFFICIENT SYNTHESIS OF 3-ALKYLIDENEPHTHALIDES, γ-ALKYLIDENEBUTENOLIDES AND γ-ALKYLIDENEBUTYROLACTONES
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The cyclization of 2-pentynylbenzoic acid (1a) catalyzed by various silver salts and solvents was investigated. 2-Alkynylbenzoic acids (1), 2-alken-4-ynoic acids (7), and 4-alkynoic acids (4) were effectively cyclized to the corresponding phthalides (2), γ-alkylidenebutenolides (8), and γ-alkylidenebutyrolactones (5) with silver iodide or silver as catalyst in DMF regio- and stereo-selectively in excellent yield, respectively.
- Ogawa, Yoshimitsu,Maruno, Masao,Wakamatsu, Takeshi
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p. 2587 - 2599
(2007/10/03)
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- Synthesis of Isocoumarins from o-Iodobenzoic Acid and Terminal Acetylenes Mediated by Palladium Complexes and Zinc Chloride
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o-Iodobenzoic acid (1) reacts with various terminal acetylenes (HCCR) in the presence of Pd(PPh3)4, Et3N, and ZnCl2 in DMF to give the corresponding 3-substituted isocoumarins (: R = n-C4H9 (2a); n-C3H7 (3a); CH2OCH3 (4a); C(CH3)2OH (5a); CH2OH (
- Liao, Hong-Yueh,Cheng, Chien-Hong
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p. 3711 - 3716
(2007/10/02)
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- A new synthesis of 3-ylidenephthalides via palladium-catalyzed cyclocarbonylation of 2-triflyloxyacetophenones
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The reaction of 2-triflyloxyacetophenone derivatives 1 with carbon monoxide in the presence of a palladium catalyst affords 3-ylidenephthalides 2 in good yields and under mild conditions.
- Ciattini,Mastropietro,Morera,Ortar
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p. 3763 - 3766
(2007/10/02)
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- THE CHEMISTRY OF PHTALIDE-3-CARBOXYLIC ACID - I DECARBOXYLATION ON THE PRESENCE OF THE ALDEHYDES
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The decarboxylation of phthalide-3-carboxylic acid (3-oxo-1,3-dihydroisobenzofuran-1-carboxylic acid) has been studied in the melt, in dimethylsulfoxide, and in the presence of aromatic aldehydes.The latter are efficiently trapped to produce mixtures of 3-arylidene-phthalides and 3-(arylhydroxymethyl)phthalides.Kinetic and other evidence supports the proposal that this reaction occurs in a tight cyclic transition state.
- Prager, Rolf H.,Schiesser, Carl H.
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p. 1517 - 1522
(2007/10/02)
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- PHOTOCHEMICAL ISOMERIZATIONS OF 2-PHENYL-1,3-INDANEDIONE TO E- AND Z-BENZALPHTHALIDE AND OF E-BENZALPHTHALIDE TO Z-BENZALPHTHALIDE
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The photochemical isomerizations have been studied of 2-phenyl-1,3-indanedione to mixture of E- and Z-benzalphthalide and of E-benzalphthalide to Z-benzalphthalide depending on the solvent used, concentration, and the light wavelength.The attempts at the reverse photochemical isomerization of E-benzalphthalide to 2-phenyl-1,3-indanedione have failed.Quantum yields of the isomerization of 2-phenyl-1,3-indanedione decrease in the following solvent series : cyclohexane > acetonitrile ca. benzene > tetrachloromethane >> methanol.The isomerization quantum yield of2-phenyl-1,3-indanedione is inversely proportional to concentration of the starting substance, but the dependence of 1/Φ on the concentration is not linear.
- Gaplovsky, Anton,Donovalova, Jana,Hrnciar, Pavel
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p. 1569 - 1576
(2007/10/02)
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- Synthesis of 1,2,3,9b-Tetrahydro-9b-hydroxy-1-phenylpyrroloisoindol-5-one via the Hydrazinolysis of 2-Phenyl-2-(2-phthalimidoethyl)indan-1,3-dione
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Hydrazinolysis of 2-phenyl-2-(2-phthalimidoethyl)indan-1,3-dione gave 1,2,3,9b-tetrahydro-9b-hydroxy-1-phenylpyrroloisoindol-5-one via the conversion of 2-(2-aminoethyl)-2-phenylindan-1,3-dione into the carbinolamine which underwent ring expansion followed by a transannular cyclisation.
- Crabb, Trevor A.,Patel, Ansuya,Newton, Roger F.,Price, Barry J.,Tucker, Michael J.
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p. 2783 - 2786
(2007/10/02)
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- Benzalphthalides and broad spectrum sun screens
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Compositions containing a benzalphthalide, i.e. benzalphthalide or a substituted benzalphthalide, are very effective broad spectrum sun screens. They are prepared by reacting substituted or unsubstituted phthalic anhydride with the corresponding substituted or unsubstituted phenyl acetic acid.
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