- Ring construction of several heterocycles with phosphorus pentoxide-methanesulfonic acid (PPMA)
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The cyclization reactions with CH3SO3H/P2O5 (PPMA) or CF3SO3H/P2O5 (PPTMA) at 80-100°C for 3-10 min afforded several heterocycles (6, 7-dihydropyrrolo[2, 3-c]azepin-4,8(1H, 5H)-dione, 4-oxo-4,5,6,7-tetrahydrothianaphthene, carbostyril derivatives).
- Cho, Hidetsura,Matsuki, Shinsuke
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Read Online
- Efficient synthesis of 1-tetralones from 4-arylbutyric acids by combined use of solid acid catalysts and microwave irradiation
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Solid acid catalysts such as H-Beta zeolites effectively promote dehydrative intramolecular cyclization of 4-arylbutyric acids under microwave irradiation to give 1-tetralone derivatives in high yields. Copyright
- Hiroki, Kazuaki,Hatori, Makiko,Yamashita, Hiroshi,Sugiyama, Jun-Ichi
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Read Online
- Sustainable flow oppenauer oxidation of secondary benzylic alcohols with a heterogeneous zirconia catalyst
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A flow chemistry process for the Oppenauer oxidation of benzylic secondary alcohols using partially hydrated zirconium oxide and a simple carbonyl containing oxidant such as acetone, cyclohexanone, and neopentanal is reported. The heterogeneous oxidative system could be applied to a wide range of functionalized alcohol substrates, allowing clean and fast delivery of ketone products within a few minutes between 40 and 100 C.
- Chorghade, Rajeev,Battilocchio, Claudio,Hawkins, Joel M.,Ley, Steven V.
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Read Online
- Chemoselective Oxidation of Equatorial Alcohols with N-Ligated λ3-Iodanes
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The site-selective and chemoselective functionalization of alcohols in complex polyols remains a formidable synthetic challenge. Whereas significant advancements have been made in selective derivatization at the oxygen center, chemoselective oxidation to the corresponding carbonyls is less developed. In cyclic systems, whereas the selective oxidation of axial alcohols is well known, a complementary equatorial selective process has not yet been reported. Herein we report the utility of nitrogen-ligated (bis)cationic λ3-iodanes (N-HVIs) for alcohol oxidation and their unprecedented levels of selectivity for the oxidation of equatorial over axial alcohols. The conditions are mild, and the simple pyridine-ligated reagent (Py-HVI) is readily synthesized from commercial PhI(OAc)2 and can be either isolated or generated in situ. Conformational selectivity is demonstrated in both flexible 1,2-substituted cyclohexanols and rigid polyol scaffolds, providing chemists with a novel tool for chemoselective oxidation.
- Mikhael, Myriam,Adler, Sophia A.,Wengryniuk, Sarah E.
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supporting information
p. 5889 - 5893
(2019/08/26)
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- Hydrogen bond donor solvents enabled metal and halogen-free Friedel–Crafts acylations with virtually no waste stream
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We have developed a metal and halogen-free Friedel–Crafts acylation protocol with virtually no waste stream generation. We propose a hydrogen bonding donor solvent will form a hydrogen bonding network and may provide significant rate enhancement for Friedel–Crafts reactions. Trifluoroacetic acid is one of the strongest H-bond donor solvents, which is also volatile and can be easily recovered by distillation without need for reaction workup. Our protocol is a ‘green’ Friedel–Crafts acylation process: 1) the catalyst can be recovered and reused; 2) using halogen free starting material (carboxylic acids anhydride or carboxylic acids); 3) no need for aqueous reaction work-up; 4) minimum or no waste steam generation.
- Liu, Guangchang,Xu, Bo
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supporting information
p. 869 - 872
(2018/02/09)
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- NOVEL TRICYCLIC CALCIUM SENSING RECEPTOR ANTAGONISTS
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Novel tricyclic compounds of Formula (I) and pharmaceutically acceptable salts thereof are disclosed as useful for treating or preventing osteoporosis and similar conditions. The compounds are effective as calcium sensing receptor antagonists. Pharmaceutical compositions and methods of treatment are also included.
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- NOVEL TRICYCLIC CALCIUM SENSING RECEPTOR ANTAGONISTS FOR THE TREATMENT OF OSTEOPOROSIS
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Novel tricyclic compounds of the formula (I): and pharmaceutically acceptable salts thereof are disclosed as useful for treating or preventing osteoporosis and similar conditions. The compounds are effective as calcium sensing receptor antagonists. Pharmaceutical compositions and methods of treatment are also included.
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- Intramolecular Friedel-Crafts Acylation Reaction Promoted by 1,1,1,3,3,3-Hexafluoro-2-propanol
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Simple dissolution of an arylalkyl acid chloride in 1,1,1,3,3,3-hexafluoro-2-propanol promotes an intramolecular Friedel-Crafts acylation without additional catalysts or reagents. This reaction is operationally trivial in both execution and product isolation (only requiring concentration followed by purification) and accommodates a broad range of substrates. Preliminary studies that bear upon potential reaction mechanisms are reported.
- Motiwala, Hashim F.,Vekariya, Rakesh H.,Aubé, Jeffrey
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p. 5484 - 5487
(2015/11/18)
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- New combination of pharmacophoric elements of potent σ1 ligands: Design, synthesis and σ receptor affinity of aminoethyl substituted tetrahydrobenzothiophenes
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The aminoethyl substituted tetrahydrobenzothiophenes 4 resulted from combination of the pharmacophoric elements of the potent σ1 ligands 2 and 3. The aminoethyl substituted tetrahydrobenzothiophenes 4 were prepared in an 8-step synthesis starting with thiophene. Whereas the σ1 affinity of the N-benzyl derivative 4a is in the medium nanomolar range (Ki = 49 nM), the analogous N-cyclohexylmethyl derivative 4d exhibits low nanomolar affinity (Ki = 5.0 nM). The reduced σ1 affinity and σ2/σ1 selectivity of tetrahydrobenzothiophenes 4 compared to analogous spirocyclic piperidines 3 is attributed to the increased conformational flexibility of the aminoethyl side chain.
- Harel, Dipak,Schepmann, Dirk,Wünsch, Bernhard
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p. 490 - 497
(2013/10/22)
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- MULTICYCLIC COMPOUNDS AND METHODS OF USE THEREOF
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Provided herein are multicyclic compounds, methods of their synthesis, pharmaceutical compositions comprising the compounds, and methods of their use. The compounds provided herein are useful for the treatment, prevention, and/or management of various neurological disorders, including but not limited to, psychosis and schizophrenia.
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Page/Page column 110
(2011/06/25)
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- SYNTHESIS OF SUBSTITUTED TETRAHYDROINDENYL COMPLEXES
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This invention relates to the synthesis of substituted tetrahydroindenyls and the use of the synthesised complexes in the homo- and co-polymerisation of ethylene and alpha-olefins.
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Page/Page column 17-19
(2010/08/04)
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- CHEMOKINE RECEPTOR ANTAGONISTS
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A compound of formula (I) or a pharmaceutically acceptable salt or prodrug ester thereof, wherein the variants R, R9, Z, X, Q and Y are defined in the specification.
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Page/Page column 208
(2010/02/13)
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- Synthesis of 1-tetralones by intramolecular Friedel-Crafts reaction of 4-arylbutyric acids using Lewis acid catalysts
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Intramolecular Friedel-Crafts reaction of 4-arylbutyric acids efficiently proceeded in the presence of catalytic amounts of Lewis acids such as Bi(NTf2)3 and M(OTf)3 (M=Bi, Ga, In and rare-earth metals) to form 1-tetralones. Chroman-4-one and thiochroman-4-one were also obtained in good yields from 3-phenoxypropionic acid and 3-phenylthiopropionic acid, respectively.
- Cui, Dong-Mei,Kawamura, Masato,Shimada, Shigeru,Hayashi, Teruyuki,Tanaka, Masato
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p. 4007 - 4010
(2007/10/03)
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- Synthesis of tri- and tetracyclic heterocycles related to cyclohexa- and cyclohepta[b]thiophenes
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Synthesis of a number of tri- and tetracyclic compounds with a fused thiophene ring starting from spiro[benzo[b]thiophene-6(5H), 1'-cycloalkyl]-4(7H)-one 1(R = H, Me, Et and n = 4, 5) and cyclohepta[b]thiophenone 2 (R1 = H, R2 = Me and R1R2 = -(CH2)4-) is described.
- Sen,Saha,Das
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p. 334 - 338
(2007/10/03)
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- New structures able to prevent the inhibition by hydroxyl radicals of glutamate transport in cultured astrocytes
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4,5,6,7-Tetrahydro-benzothiophen-7-ylamines, 4,5,6,7-tetrahydro- benzothiophen-4-ylamines, and 5,6-dihydro-4H-thieno[2,3-b] thiopyran-4- ylamines were designed, synthesized, and tested as OH radical scavengers. Most of them displayed chemical scavenging properties better than or in the same range as salicylic acid. Moreover, some compounds were able to protect in vitro the astroglial glutamate transporters against inhibitory action of radicals promoted by xanthine/xanthine oxidase. Thus, such compounds might be useful for lowering the large amounts of excitotoxic glutamate liberated during acute CNS diseases: they might protect the glutamate reuptake in astrocytes from the inhibitory action due to radicals co-liberated with glutamate.
- Cauquil-Caubere, Isoline,Kamenka, Jean-Marc
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p. 867 - 877
(2007/10/03)
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- Substituted pyrazolyl benzenesulfonamides for use in veterinary therapies
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A method of using pyrazolyl benzenesulfonamide compounds in treating inflammation and inflammation-related disorders in companion animals is disclosed.
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- Substituted pyrazolyl benzenesulfonamides for the treatment of inflammation
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A class of pyrazolyl benzenesulfonamide compounds is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula II: STR1 or a pharmaceutically-acceptable salt thereof.
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- Orally absorbable cephalosporine antibiotics. 1. Structure-activity relationships of benzothienyl- and naphthylglycine derivatives of 7-aminodeacetoxycephalosporanic acid
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A structure-activity relationship study of a number of orally absorbed cephalosporins together with their syntheses is described. These new cephalosporins are benzothienyl- and naphthylglycine derivatives of 7-aminodeacetoxycephalosporanic acid. Several different synthetic methods for the glycine side chains, their protection, and the final acylations are reported. Several of these analogues were more active than cephalexin both in vitro and r538w2 =(R)-7-(3-Benzothienylglycylamido)-3-methyl-3-cephem-4-carb oxylic in vivo against commonly encountered Gram-positive bacteria. (R)7-(3-Benzothienylglycylamido)-3-methyl-3-cephem-4-carboxylic acid has emerged as a potent antibacterial agent and is currently undergoing preclinical evaluation.
- Kukolja,Draheim,Pfeil,et al.
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p. 1886 - 1896
(2007/10/02)
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- The Synthesis of Thiophenium and Oxazolium Salts from Diazoketones
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4-Diazoacetylthianthren with perchloric acid in acetonitrile gave 2-oxo-1,2-dihydrothieno-thianthrenium perchlorate which gave the corresponding enol ether with diazomethane.This ether was compared with 3-methoxy-1-methylbenzothiophenium perchlorate, prepared from 3-methoxythiophen, and which was much more stable to solvolysis than the demethoxy-analogue.In contrast to the 4-diazoacetylthianthren, 7-diazoacetyl-2-methylbenzothiophen with acetonitrile and perchloric acid cyclized in an alternative mode to give a new synthesis of 2-methyl-4-substituted oxazolium perchlorates.
- Acheson, R. Morrin,Cooper, Martin W.
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p. 1185 - 1193
(2007/10/02)
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- Studies on Sulphur Heterocycles. Reactions of 6,7-Dihydrobenzothiophen-4(5H)one Derivatives and their Conversion to 7-Substituted Thienobenzopyran-8-ones
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Cyclization of γ-(2-thienyl)butyric acid with acid anhydrides gives 2-acyl derivatives as well as the expected 6,7-dihydrobenzothiophen-4(5H)one.Several reactions of these ketones have been studied including their conversion to O,O-diethyl thiophosphon
- Asprou, Chris M.,Brunskill, John S. A.,Jeffrey, Howard,De, Asish
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