- An efficient synthesis of oxazolines: Via a cascade reaction between azaoxyallyl cations and 1,2-benzisoxazoles
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A formal [3 + 2] cycloaddition reaction between the C and O terminals of azaoxyallyl cations formed in situ and 1,2-benzisoxazoles has been realized. This one-pot cycloaddition method provided an effective and practical pathway to synthesize oxazoline in good yields under mild conditions. The title products exhibited unique fluorescence properties.
- Sun, Li,Liu, Yi,Wang, Yankai,Li, Yuanyuan,Liu, Zhiwen,Lu, Tao,Li, Wenhai
-
supporting information
p. 7526 - 7530
(2019/08/20)
-
- [3 + 2]-Cycloaddition of Azaoxyallyl Cations with 1,2-Benzisoxazoles: A Rapid Entry to Oxazolines
-
A novel and efficient [3 + 2] cycloaddition reaction of azaoxyallyl cations and 1,2-benzisoxazoles to give oxazoline derivatives has been developed. The transformation provides a rapid entry to functionalized oxazoline scaffolds under mild and transition-metal-free conditions, which will greatly expand the reaction types of heterocycle chemistry and pave the way for syntheses of bioactive compounds.
- Feng, Juan,Zhao, Ming,Lin, Xuanzi
-
p. 9548 - 9560
(2019/08/26)
-
- Rh(II)-Catalyzed Transannulation of N-Sulfonyl-1,2,3-Triazoles with 2,1-Benzisoxazoles or 1,2-Benzisoxazoles
-
A Rh(II)-catalyzed transannulation of N-sulfonyl-1,2,3-triazoles with 2,1-benzisoxazoles has been developed, which affords an efficient method for the synthesis of quinazoline derivatives. The transformation represents an unprecedented example which utilizes N-sulfonyl-1,2,3-triazole as an aza-[2C]-component in cycloadditions. Meanwhile, a Rh(II)-catalyzed formal [3 + 2] cycloaddition of N-sulfonyl-1,2,3-triazoles with 1,2-benzisoxazoles is also presented, which enables the rapid synthesis of functionalized imidazole derivatives.
- Lei, Xiaoqiang,Gao, Mohan,Tang, Yefeng
-
supporting information
p. 4990 - 4993
(2016/10/14)
-
- Utility of Nitrogen Extrusion of Azido Complexes for the Synthesis of Nitriles, Benzoxazoles, and Benzisoxazoles
-
The utility of the nitrogen extrusion reaction of azido complexes, generated in situ from the corresponding aldehydes or ketones with TMSN3 in the presence of ZrCl4 or TfOH, has been described. These azido complexes could undergo three different pathways, depending on the substrates. First, azido methanolate complexes or imine diazonium ions could lead to benzisoxazole products via an intramolecular nucleophilic substitution. Second, imine diazonium ions could also undergo either the elimination of proton to provide nitrile products in good to excellent yields or an aryl migration, followed by an intramolecular nucleophilic addition, to give benzoxazole products in good yields.
- Nimnual, Phongprapan,Tummatorn, Jumreang,Thongsornkleeb, Charnsak,Ruchirawat, Somsak
-
p. 8657 - 8667
(2015/09/15)
-
- Chromatography-free entry to substituted salicylonitriles: Mitsunobu-triggered domino reactions of salicylaldoximes
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A mild and efficient one-pot procedure is described to transform salicylaldoximes into salicylonitriles using Mitsunobu chemistry. The reactions proceed through the corresponding 1,2-benzisoxazoles that undergo the Kemp elimination in situ to generate the
- Whiting, Ellis,Lanning, Maryanna E.,Scheenstra, Jacob A.,Fletcher, Steven
-
p. 1229 - 1234
(2015/01/30)
-
- Triflic anhydride: A mild reagent for highly efficient synthesis of 1,2-benzisoxazoles, isoxazolo, and isothiazolo quinolines without additive or base
-
The synthetic utility of trifluoromethanesulphonic anhydride (triflic anhydride, TA) without additive or base for the high-yielding synthesis of a wide variety of 1,2-benzisoxazoles from 2-hydroxyaryl aldoximes and ketoximes under mild conditions has been carried out for the first time. As a continuation of our study, syntheses of isoxazolo and isothiazolo quinolones have also been demonstrated using triflic anhydride under similar conditions. This method is simple and has benefits from the easy way to isolate the products in excellent yields.
- Kalkhambkar, Rajesh G.,Yuvaraj
-
supporting information
p. 547 - 555
(2014/01/23)
-
- Gallium-containing polymer brush film as efficient supported Lewis acid catalyst in a glass microreactor
-
Polystyrene sulfonate polymer brushes, grown on the interior of the microchannels in a microreactor, have been used for the anchoring of gallium as a Lewis acid catalyst. Initially, gallium-containing polymer brushes were grown on a flat silicon oxide surface and were characterized by FTIR, ellipsometry, and X-ray photoelectron spectroscopy (XPS). XPS revealed the presence of one gallium per 2-3 styrene sulfonate groups of the polymer brushes. The catalytic activity of the Lewis acid-functionalized brushes in a microreactor was demonstrated for the dehydration of oximes, using cinnamaldehyde oxime as a model substrate, and for the formation of oxazoles by ring closure of ortho-hydroxy oximes. The catalytic activity of the microreactor could be maintained by periodic reactivation by treatment with GaCl3.
- Munirathinam, Rajesh,Ricciardi, Roberto,Egberink, Richard J.M.,Huskens, Jurriaan,Holtkamp, Michael,Wormeester, Herbert,Karst, Uwe,Verboom, Willem
-
p. 1698 - 1704
(2013/10/22)
-
- Heterogeneous catalytic method for the conversion of aldoximes into nitriles using molecular sieve modified with Copper(II)
-
A simple heterogeneous metal-catalyzed method was developed for the transformation of aldoximes into nitriles. Molecular sieve (4 A) modified with copper(II) proved to be an efficient catalyst for the conversion. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.
- Kiss, Arpad,Hell, Zoltan
-
supporting information
p. 1778 - 1786
(2013/05/22)
-
- Reaction of triflyl-imidazole with aldoximes: Facile synthesis of nitriles and formation of novel aldoxime-bis(N-triflyl)-imidazole adducts
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The synthetic utility of N-triflylimidazole as an in situ reagent for facile, high yielding, synthesis of various aliphatic, aromatic, and heteroaromatic nitriles from the corresponding aldoximes has been demonstrated. With benzaldoximes, in the presence of certain substitutents (2-F; 2-OMe; 3-CF3; 2-Me-5-F) a different course of reaction was observed, leading instead to novel 1:1 aldoxime-bis(N-triflyl)imidazole covalent adducts, in which the aldoxime oxygen atom is bonded to the imidazole C-2 ring carbon. For these aldoximes, conversion to nitrile could be effected by reaction with Tf2O in the absence of imidazole. The molecular structure of the adduct formed from 2-methyl-5-fluoro-benzaldoxime was confirmed by X-ray analysis. Plausible mechanisms for the formation of 1:1 covalent adducts have been considered. Various attempts to isolate such adducts via the reaction of an authentic sample of bis(N-triflyl)imidazolium trifate with aldoxime were unsuccessful. Remarkably, whereas isolated benzaldoxime adducts undergo deprotonation/methylation with NaH/MeI, an authentic sample of bis(N-triflyl)imidazolium triflate did not undergo H/Me exchange under these conditions. These transformations are discussed.
- Kalkhambkar, Rajesh G.,Bunge, Scott D.,Laali, Kenneth K.
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supporting information; experimental part
p. 5184 - 5187
(2011/10/13)
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- ALKYL-SUBSTITUTED 3' COMPOUNDS HAVING 5-HT6 RECEPTOR AFFINITY
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The present disclosure provides compounds having affinity for the 5-HT6 receptor which are of the formula (I): wherein R1, R2, Ar, m and n are as defined herein. The disclosure also relates to methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.
- -
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Page/Page column 30
(2010/02/17)
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- CONDENSED HETEROCYCLIC COMPOUNDS HAVING 5-HT6 RECEPTOR AFFINITY
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The present disclosure provides compounds having affinity for the 5-HT6 receptor which are of the formula (I) wherein R1, A, B, D, E, G, Q, Ar, n, m, and p are as defined herein. The disclosure also relates to methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.
- -
-
Page/Page column 91
(2010/04/03)
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- ACYCLIC COMPOUNDS HAVING 5-HT6 RECEPTOR AFFINITY
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The present disclosure provides compounds having affinity for the 5-HT6 receptor which are of the formula (I): wherein R1, R2, R5, Q, G, Ar, m, and n are as defined herein. The disclosure also relates to methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.
- -
-
Page/Page column 60
(2010/03/02)
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- 4'-AMINO CYCLIC COMPOUNDS HAVING 5-HT6 RECEPTOR AFFINITY
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The present disclosure provides compounds having affinity for the 5-HT6 receptor which are of the formula (I): formula (I) wherein Cy is selected from formula (Il) and wherein R1, R2, R3, Q, G, Ar, m, n and p are as defined herein. The disclosure also relates to methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.
- -
-
Page/Page column 109
(2010/04/06)
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- PYRROLIDINE-SUBSTITUTED AZAINDOLE COMPOUNDS HAVING 5-HT6 RECEPTOR AFFINITY
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The present disclosure provides compounds having affinity for the 5-HT6 receptor which are of the formula (I): wherein R1, R2, A, B, D, E, G, Ar, and n are as defined herein. The disclosure also relates to methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.
- -
-
Page/Page column 40
(2010/02/17)
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- 3' SUBSTITUTED COMPOUNDS HAVING 5-HT6 RECEPTOR AFFINITY
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The present disclosure provides compounds having affinity for the 5-HT6 receptor which are of the formula (I): wherein Q, R1, R4, m and Ar are as defined herein. The disclosure also relates to methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.
- -
-
Page/Page column 126-127
(2009/04/25)
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- 4' SUBSTITUTED COMPOUNDS HAVING 5-HT6 RECEPTOR AFFINITY
-
The present disclosure provides compounds having affinity for the 5-HT6 receptor which are of the formula (I): wherein R1, R2, R5, R6, B, D, E, G, Q, x and n are as defined herein. The disclosure also relates to methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.
- -
-
Page/Page column 28
(2009/01/24)
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- 6' SUBSTITUTED COMPOUNDS HAVING 5-HT6 RECEPTOR AFFINITY
-
The present disclosure provides compounds having affinity for the 5-HT6 receptor which are of the formula (I): wherein R1—R4 A, B, D, E, and G are as defined herein. The disclosure also relates to methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.
- -
-
Page/Page column 51
(2008/12/08)
-
- COMPOUNDS HAVING 5-HT6 RECEPTOR AFFINITY
-
The present disclosure provides compounds having affinity for the 5HT6 receptor which are of the formula (I), wherein R1-R3 A, B, D, E, G, Q, and x are as defined herein. The disclosure also relates to methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.
- -
-
Page/Page column 138; 139
(2010/11/28)
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- A novel method for the highly efficient synthesis of 1,2-benzisoxazoles under neutral conditions using the Ph3P/DDQ system
-
The use of Ph3P/DDQ offers a novel, neutral and highly efficient method for the efficient conversion of 2-hydroxyaryl aldoximes and ketoximes to 1,2-benzisoxazoles in excellent yields at room temperature.
- Iranpoor, Nasser,Firouzabadi, Habib,Nowrouzi, Najmeh
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p. 8247 - 8250
(2007/10/03)
-
- Substituted amino methyl factor Xa inhibitors
-
The present application describes substituted-aminomethyl substituted compounds and derivatives thereof, or pharmaceutically acceptable salt forms thereof, which are useful as inhibitors of factor Xa.
- -
-
-
- Heteroaryl-phenyl substituted factor Xa inhibitors
-
The present application describes heteroaryl-phenyl substituted compounds and derivatives thereof, or pharmaceutically acceptable salt or prodrug forms thereof, which are useful as inhibitors of factor Xa.
- -
-
-
- Heteroaryl- phenyl heterobicyclic factor Xa inhibitors
-
The present application describes heteroaryl-phenyl heterobicycles and derivatives thereof, or pharmaceutically acceptable salt forms thereof, which are useful as inhibitors of factor Xa.
- -
-
-
- Alkyl, alkenyl and alkynyl Chrysamine G derivatives for the antemortem diagnosis of Alzheimer's disease and in vivo imaging and prevention of amyloid deposition
-
Amyloid binding compounds which are non-azo derivatives of Chrysamine G, pharmaceutical compositions containing, and methods using such compounds to identify Alzheimer's brain in vivo and to diagnose other pathological conditions characterized by amyloidosis, such as Down's Syndrome are described. Pharmaceutical compositions containing non-azo derivatives of Chrysamine G and methods using such compositions to prevent cell degeneration and amyloid-induced toxicity in amyloidosis associated conditions are also described. Methods using non-azo Chrysamine G derivatives to stain or detect amyloid deposits in biopsy or post-mortem tissue are also described. Methods using non-azo Chrysamine G derivatives to quantify amyloid deposits in homogenates of biopsy and post-mortem tissue are also described.
- -
-
-
- Benzimidazolinones, benzoxazolinones, benzopiperazinones, indanones, and derivatives thereof as inhibitors of factor Xa
-
The present application describes inhibitors of factor Xa of formula I: or pharmaceutically acceptable salt forms thereof, wherein W, W1, W2, and W3may be N or C and J, Ja, and Jbcombine to form a substituted carbocycle or heterocycle.
- -
-
-
- Benzisoxazole-derived antidiabetic compounds
-
The instant invention is concerned with acetylphenols which are useful as antiobesity and antidiabetic compounds. Compositions and methods for the use of the compounds in the treatment of diabetes and obesity and for lowering or modulating triglyceride levels and cholesterol levels or raising high density lipoprotein levels or for increasing gut motility or for treating atherosclerosis are also disclosed.
- -
-
-
- Non-porphyrin compound for use as a diagnosticum and/or pharmaceutical
-
The invention relates to a non porphyrin compound or a pharmaceutically acceptable salt thereof, suitable for in vitro, in vivo and/or ex vivo use as a diagnosticum and/or pharmaceutical, said compound comprising:a targeting agent for targeting a specific area, such as an organ and/or tissue,a labelling agent L for labelling the targeted area; said targeting agent being connected to the labelling agent L, wherein said targeting agent comprises one or more substituted and/or unsubstituted organic ring compounds.
- -
-
-
- 6-membered aromatics as factor Xa inhibitors
-
The present application describes 6-membered aromatics of formula I: or pharmaceutically acceptable salt forms thereof, wherein D may be CH2NH2 or C(=NH)NH2, which are useful as inhibitors of factor Xa.
- -
-
-
- α-branched anilines, toluenes, and analogs thereof as factor Xa inhibitors
-
The present application describes m-amidino phenyl analogs of formula I: wherein D can be amidino and E can be phenyl, which are useful as inhibitors of factor Xa.
- -
-
-
- N-(AMIDINOPHENYL) CYCLOUREA ANALOGS AS FACTOR XA INHIBITORS
-
The present application describes N-(amidinophenyl)cyclourea analogs of formula I: STR1 which are useful as inhibitors of factor Xa.
- -
-
-
- INHIBITORS OF FACTOR XA WITH A NEUTRAL P1 SPECIFICITY GROUP
-
The present application describes inhibitors of factor Xa with a neutral P1 specificity group of formula I: STR1 or pharmaceutically acceptable salt forms thereof, wherein R and E may be groups such as methoxy and halo.
- -
-
-
- A simple and convenient synthesis of 1,2-benzoxazoles via intramolecular Mitsunobu reaction from salicylaldoximes and orthohydroxyarylketoximes
-
Various substituted 1,2-benzoxazoles were prepared with good yields from salicylaldoximes and orthohydroxyphenylketoximes via intramolecular Mitsunobu reaction.
- Poissonnet, Guillaume
-
p. 3839 - 3846
(2007/10/03)
-
- METHODS OF USING PIPERIDYL-BENZISOXAZOLE AND BENISOTHIAZOLE DERIVATIVES AS CHOLINESTERASE INHIBITORS
-
Disclosed herein are compounds of the formula wherein R1 R2, R7, R8, X, Y, M and L are defined as below The compounds of formula I are cholinesterase inhibitors and are useful in enhancing memory in patients suffering from dementia and Alzheimer's disease
- -
-
-
- Kinetics and Mechanism of Intramolecular Cyclocondensation of Potassium Oxime-O-Sulfonates of 2-Hydroxybenzenecarbonyl Compounds to Benzazols
-
The effects of pH, buffer concentration and temperature on conversion rate of potassium oxime-O-sulfonates of 2-hydroxybenzaldehyde and 2-hydroxyacetophenone to benzisoxazole or 2-methylbenzoxazole, respectively, were examined.The mechanisms of both reactions have been proposed. Key words: oxime-O-sulfonic acids of 2-hydroxybenzenecarbonyl compounds, cyclocondensation, kinetics, mechanism
- Suwinski, J.,Walczak, K.
-
p. 1267 - 1273
(2007/10/02)
-
- SYNTHESIS OF ISOXAZOLE DERIVATIVES IN REACTION OF 2-HYDROXYPHENYLCARBONYL COMPOUNDS OR 1,3-DIKETONES WITH HYDROXYLAMINE-O-SULFONIC ACID
-
2-Hydroxybenzaldehyde 1a and 2-hydroxyacetophenone 1b react with hydroxylamine-O-sulfonic acid (HSA) yielding the corresponding oxime hydrogensulfates 2a and 2b, separated as potassium salts.These salts undergo conversion with good yields to benzisoxazole 3a and 2-methylbenzoxazole 3b, respectively.In similar reaction of 1,3-diketones, both cyclic and acyclic 1c-k with HSA, isoxazole derivatives 3c-k were obtained.
- Suwinski, J.,Walczak, K.
-
p. 777 - 785
(2007/10/02)
-
- Pyrolyses of o-Alkoxy- and o-Alkylthio-N-Allylanilines and of Some Related O- and S-Allyl Compounds
-
The o-substituted allyl compounds (1)-(12) have been pyrolysed in order to generate aminyl, phenoxyl, and thiophenoxyl radicals with adjacent substituents.In all cases, products are formed by intramolecular hydrogen transfer from the substituent to the radical centre.This process may be followed by rearrangement to give an aldehyde, by heteroatom extrusion to give an alkene, or by ring formation to give five-membered ring heterocycles (Scheme 1, routes A, B1, and B2 respectively.The distribution of products formed by each route is dependent both on the nature of the o-substituent, and on the nature of the initial radical.
- Cadogan, J. I. G.,Hickson, Clare L.,McNab, Hamish
-
p. 1885 - 1890
(2007/10/02)
-
- Reactive Nitrogenous Molecules from Meldrum's Acid Derivatives, Pyrrole-2,3-diones, and Isoxazolones
-
Flash vacuum pyrolysis of 5-(aminomethylidene)-2,2-dimethyl-1,3-dioxane-4,6-diones (Meldrum's acid derivatives) 12 gives 4-hydroxyquinolines/4-quinolones 15 or 3-enaminoacroleins 22 in good to excellent yields.Intermediate (aminomethylene)ketenes and imidoylketenes are directly observed and their transformation into product 22 monitored by low-temperature IR spectroscopy.Imidoylketenes are also formed and observed upon thermal CO extrusion from pyrrole-2,3-diones 16.Isocyanoamines and fulminates are generated by pyrolysis of hydrazono- or oximino-Meldrum's acid derivatives 32 and 39, monitored by IR spectroscopy, and found to rearrange to cyanamides and cyanates, depending on substituents.The thermal reactions of isoxazol-5(4H)-ones and Meldrum's acid derivatives are compared and discussed.
- Briehl, Horst,Lukosch, Adelheid,Wentrup, Curt
-
p. 2772 - 2779
(2007/10/02)
-
- Organic Fulminates, R-O-NC
-
Organic fulminates are generated by flash vacuum pyrolysis and matrix photolysis of 4-oximinoisoxazol-5(4H)-ones.
- Wentrup, Curt,Gerecht, Bernd,Laqua, Dieter,Briehl, Horst,Winter, Hans-Wilhelm,et al.
-
p. 1046 - 1048
(2007/10/02)
-
- CATALYSE ET INHIBITION DE DEUX REACTIONS CONCURRENTES EN MILIEU MICELLAIRE CATIONIQUE
-
The general acid catalysed hydrolysis and the intramolecular nucleophilic anionic cyclization of acyloximes operate concurrently in water at pH 7-9.Hydrolysis is inhibited by cationic micelles; changing the length of the acyl chain does not affect the micellar effect, possibly because the environment of the reacting species is not influenced by this variation in the structure of the micelle.
- Soto, R.,Meyer, G.,Viout, P.
-
p. 2977 - 2982
(2007/10/02)
-
