cas 3141-93-3, 3',4'-DIMETHOXY-2-PHENYLACETOPHENONE

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Regioselection in the synthesis of 4-benzyltetral-1-ones and the new 4-arylbenzosuber-1-ones
The intramolecular Friedel-Crafts acylation of 4,5-diarylpentanoic acids has the possibility to cyclise to either a 6-membered ring to give 4-benzyltetral-1-one or a 7-membered ring to give 4-arylbenzosuber-1-one. Of these, only the former compound class has previously been reported. The impact of the substituents positioning on the outcome of the cyclisation has been investigated. The complete formation of either the tetralone or the benzosuberone regioisomer was possible under the same reaction conditions, dependent upon the ring activation and/or deactivation of the chosen substituents. Selected bromo or methoxy substituents could be used as auxiliaries, included in precursors to afford the desired regioisomer and then subsequently removed.
Truong, Daniel,Howard, Brittany L.,Thompson, Philip E.
(2021/03/09)

Benzylic aroylation of toluenes with unactivated tertiary benzamides promoted by directed ortho-lithiation
The deprotonative functionalization of toluenes, for their weak acidity, generally needs strong bases, thus leading to the requirement of harsh conditions and the generation of by-products. Direct nucleophilic acyl substitution reaction of amides with organometallic reagents could provide an ideal solution for ketone synthesis. However, the inert amides and highly reactive organometallic reagents bring great challenges for an efficient and selective synthetic approach. Herein, we reported an lithium diisopropylamide (LDA)-promoted benzylic aroylation of toluenes with unactivated tertiary benzamides, providing a direct and efficient synthesis of various aryl benzyl ketones. This process features a kinetic deprotonative functionalization of toluenes with a readily available base LDA. Mechanism studies revealed that the directed ortho-lithiation of the tertiary benzamide with LDA promoted the benzylic kinetic deprotonation of toluene and triggered the nucleophilic acyl substitution reaction with the amide. [Figure not available: see fulltext.].
Bao, Can-Can,Luo, Yan-Long,Du, Hui-Zhen,Guan, Bing-Tao
p. 1349 - 1354
(2021/07/12)

Palladium-catalyzed denitrative α-arylation of ketones with nitroarenes
The palladium-catalyzed α-arylation of ketones with readily available nitroarenes and nitroheteroarenes provides access to useful α-aryl and α-heteroaryl ketones. The use of the Pd/ BrettPhos catalysts was critical to achieve high efficiency for these transformations, whereas other catalysts led to decreased yields or no conversions. The intramolecular type substrate was also applied in this methodology and gave a chromone derivative. Polyaromatic carbonyl compounds can be easily obtained by multicomponent tandem reactions, via nucleophilic aromatic substitution (SNAr) or cross-coupling reaction followed by this denitrative arylation. Kinetic experiments show that the electronic effect of nitrobenzenes has a greater effect on the reaction rate than the electronic effect of ketones.
Li, Zhirong,Peng, Yonggang,Wu, Tao
supporting information

(2021/02/16)

Metal-free synthesis of ketones by visible-light induced aerobic oxidative radical addition of aryl hydrazines to alkenes
A green and cost-effective method has been developed for the conversion of alkenes to ketones under metal-free conditions. The reaction involves the oxidative addition of alkenes with aryl radicals, which are generated by visible-light induced aerobic oxidation of arylhydrazines. The key features of this reaction include broad substrate scope, readily available reagents and amenability to gram-scale synthesis.
Ding, Ya,Zhang, Wenkai,Li, Hao,Meng, Yunge,Zhang, Te,Chen, Qiu-Yun,Zhu, Chunyin
supporting information
p. 2941 - 2944
(2017/07/24)

Rh(III)-catalyzed C-H activation/cyclization of oximes with alkenes for regioselective synthesis of isoquinolines
A Rh(iii)-catalyzed C-H activation/cyclization of oximes and alkenes for facile and regioselective access to isoquinolines has been developed. This protocol features mild reaction conditions and easily accessible starting materials, and has been applied to the concise synthesis of moxaverine. A kinetic isotope effect study was conducted and a plausible mechanism was proposed.
Chen, Renjie,Qi, Jifeng,Mao, Zhenjun,Cui, Sunliang
p. 6201 - 6204
(2016/07/11)

Synthesis of substituted phenanthrofurans
A three-step protocol toward phenanthrofurans 1 starting with deoxybenzoins 3 is developed with moderate to good yield. A facile process is carried out for the (1) α-propargylation of 3 with NaH and propargyl bromide 2 in refluxing THF, (2) Bi(OTf)3-mediated cycloisomerization of γ-ynones 4 with 4 ? molecular sieves in MeNO2 at rt, and (3) photolytic Scholl annulation of 2,3-diarylfurans 5 with I2 in EtOAc at rt. The key structures of 1 are confirmed by X-ray crystallographic analysis.
Chan, Chieh-Kai,Chen, Yi-Chia,Chen, Yeh-Long,Chang, Meng-Yang
p. 9187 - 9195
(2015/11/27)

An unusual chemoselective oxidation strategy by an unprecedented exploration of an electrophilic center of DMSO: A new facet to classical DMSO oxidation
A conceptually new dimethyl sulfoxide (DMSO) based oxidation process without the use of any activator has been demonstrated for the oxidation of active methylenes and benzhydrols. The developed protocol utilizes the electrophilic center of DMSO for oxidation, which was unexplored before. Mechanistic investigation has confirmed that the source of oxygen is DMSO.
Chebolu, Rajesh,Bahuguna, Ashish,Sharma, Reena,Mishra, Vivek Kumar,Ravikumar
supporting information
p. 15438 - 15441
(2015/10/20)

Hexaphenylbenzene-based polymers of intrinsic microporosity
Microporous polymers derived from the 1,2- and 1,4-regioisomers of di(3′,4′-dihydroxyphenyl)tetraphenylbenzene have very different properties with the former being composed predominantly of cyclic oligomers whereas the latter is of high molar mass suitable for the formation of robust solvent-cast films of high gas permeability.
Short, Rhys,Carta, Mariolino,Bezzu, C. Grazia,Fritsch, Detlev,Kariuki, Benson M.,McKeown, Neil B.
p. 6822 - 6824
(2011/08/08)

Simple route to 3-(2-indolyl)-1-propanones via a furan recyclization reaction
A simple route to 1-R-3-(2-indolyl)-1-propanones has been elaborated based on recyclization of 2-(2-aminobenzyl)furan derivatives. Being a modification of the Reissert indole synthesis, our approach employs the furan ring as a source of carbonyl function. This approach is general and allows varying of substituents in aromatic ring as well as in 3-position of indole nucleus.
Butin, Alexander V.,Smirnov, Sergey K.,Stroganova, Tatyana A.,Bender, Wolfgang,Krapivin, Gennady D.
p. 474 - 491
(2007/10/03)

Synthesis of new 1,2-Diphenyl-4, 5-dihydro-3H-3-benzazepines
1,2-Diphenyl-4,5-dihydro-3H-3-benzazepine derivatives (2a-d) were synthesized via cyclization reaction of N-[2-(2-iodophenyl)ethyl]-α-phenylphenacylamines (5a-c) and (5e) with n-C4H9Li, followed by dehydration of the cyclization prod
Kaito, Chiaki,Sakamoto, Kumiko,Sakamoto, Mitsushi,Yamauchi, Aiko,Kihara, Masaru
p. 2319 - 2326
(2007/10/03)

Towards a facile synthesis of triarylethanones: Palladium-catalyzed arylation of ketone enolates under homogeneous and heterogeneous conditions
The palladium-catalyzed regioselective α-monoarylation of deoxybenzoins and α,α-diarylation of acetophenones provides general, efficient access to 1,2,2-triarylethanones. After a comprehensive search for suitable experimental conditions to optimize such transformations, both reactions are alternatively conducted by means of either commercially available polymer-anchored catalysts or a very simple homogeneous catalytic system, thus avoiding the use of complex ligands. In addition, the synthesis of deoxybenzoins employing polymer-supported fibrous palladium catalysts is reported for the first time, and the excellent catalyst recycling properties suggest applicability to industrial purposes.
Churruca, Fátima,SanMartin, Raul,Carril, Mónica,Tellitu, Imanol,Domínguez, Esther
p. 2393 - 2408
(2007/10/03)

Catecholamine surrogates useful as β3 agonists
Compounds of the formula STR1 or pharmaceutically acceptable salts thereof wherein: A is a bond, --(CH 2) n -- or --CH(B)--, where n is an integer of 1 to 3 and B is --CN, --CON(R 9)R 9'' or --CO 2 R 7 ;R 1 is lower alkyl, aryl or arylalkyl;R 2 is hydrogen, hydroxy, alkoxy, --CH 2 OH, cyano, --C(O)OR 7, --CO 2 H, --CONH 2, tetrazole, --CH 2 NH 2 or halogen; STR2 R 3 is hydrogen, alkyl, heterocycle or R 4 is hydrogen, alkyl or B;R 5, R 5'', R 8, R 8'' or R 8"" are independently hydrogen, alkoxy, lower alkyl, halogen, --OH, --CN, --(CH 2) n NR 6 COR 7, --CON(R 6)R 6'', --CON(R 6)OR 6'', --CO 2 R 6, --SR 7, --SOR 7, --SO 2 R 7, --N(R 6)SO 2 R 1, --N(R 6)R 6'', --NR 6 COR 7, --OCH 2 CON(R 6)R 6'', --OCH 2 CO 2 R 7 or aryl; orR 5 and R 5'' or R 8 and R 8'' may together with the carbon atoms to which they are attached form an aryl or heterocycle;R 6 and R 6'' are independently hydrogen or lower alkyl; andR 7 is lower alkyl;R 9 is hydrogen, lower alkyl, alkyl, cycloalkyl, arylalkyl, aryl, heteroaryl; or R 9 and R 9'' may together with the nitrogen atom to which they are attached form a heterocycle; with the proviso that when A is a bond or --(CH 2) n and R 3 is hydrogen or unsubstituted alkyl, then R 4 is B or substituted alkyl. These compounds are beta 3 adrenergic receptor agonists and are useful, therefore for example, in the treatment of diabetes, obesity and gastrointestinal diseases.
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(2008/06/13)

UNSYMMETRICALLY SUBSTITUTED DEOXYBENZOINS: AN IMPROVED PREPARATIVE ROUTE
A regioselective synthesis of unsymmetrically substituted deoxybenzoins via α-aminonitriles, establishing the advantage of the use of N,N-dimethylaminonitriles over the corresponding N,N-diethylamino derivatives, is reported.
Badia, D.,Dominguez, E.,Galarza, J.,Lete, E.,Marigorta, E. Martinez de,Villa, M. J.
p. 77 - 82
(2007/10/02)

Syntheses og Stilbenes with a C2-Sidechain in o-Position and of their Deuteriated Analogues
Syntheses of o-(β-aminoethyl)-stilbene-urethanes (types 1, 2 and 3) and o-(β-phenethyl)-stilbenes 4 are described.The urethanes are obtained by degradation of 1-benzyl-1,2,3,4-tetrahydroisoquinolines with ethylchloroformate; 4 is synthesized by reduction of desoxybenzoines, followed by o-formylation and Wittig-reaction.The deuteriated isotopomers were obtained via the corresponding deuteriated precursors. - Keywords: Stilbenes, o-substituted; Deuteriated compounds
Mayer, Klaus K.,Prior, Silvia,Wiegrebe, Wolfgang
p. 511 - 532
(2007/10/02)

o-Aminophenyl Alkyl/Aralkyl Ketones and Their Derivatives: Part IV - Synthesis of 4-Benzyl-6,7-dimethoxyquinazoline
o-Nitrophenyl benzyl ketones (II) have been exclusively synthesised from the corresponding substituted α-(o-nitroaroyl)arylacetaldehydes by the acid-catalysed deformylation.Nitration of deoxybenzoins having one of the benzene nuclei activated, such as the
Kamath, H. V.,Dhekne, Vijay V.,Kulkarni, Sheshgiri N.
p. 911 - 913
(2007/10/02)

The Photochemistry of the Host-Guest Complex. V. The Effect of the Sodium Ion on the Photoreaction of Benzil Derivatives with a Crown Ether Moiety
The photolysis of 4'-(2-phenyl-1,2-dioxoethyl)benzo-15-crown-5 in benzene containing 1-dodecanethiol gives benzaldehyde and 4'-formylbenzo-15-crown-5.The formation of the aldehydes was inhibited by the sodium ion, whereas the photolysys of 1-(3,4-dimethoxyphenyl)-2-phenylethanedione was not inhibited by the sodium ion.This inhibition must be due to the decrease in the formation of benzoyl radicals from the triplet excited state of the crown ether derivative.The salt effect was discussed on the basis of the spectral data.
Hirano, Hideki,Kurumaya, Katsuyuki,Tada, Masaru
p. 2708 - 2711
(2007/10/02)

Synthetic Uses of Open-Chain Analogues of Reissert Compounds
Open-chain analogues, 2, of Reissert compounds are readily obtained by reaction of cyanohydrins with primary amines, the resulting aminonitriles, 1, then being acylated.Hydrofluoroborate salts, 3, of 2 are prepared by reaction with fluoroboric acid in glacial acetic acid.The salts, 3, undergo 1,3-dipolar addition reactions with reactive alkynes to give substituted pyrroles and with ethyl acrylate to give a different type of substituted pyrrole, the initial step in this instance being a Diels-Alder reaction.The open-chain Reissert analogues 2 also undergo base-catalyzed reactions, such as alkylation to provide compounds 22, which, in turn, undergo cleavage reactions in ethanolic alkali to give ketones 23.A conjugate addition reaction of the anion 18 to methyl acrylate to give, after some subsequent steps, a substituted pyrrole, 9, has also been demonstrated. α-Anilino ketones 27 result when the anion 18 is caused to react with aldehydes, the initial reaction mixtures being subjected to subsequent alkaline hydrolysis.Finally, N-benzyl Reissert analogues have been found to give desoxybenzoins plus benzonitriles on treatment with sodium hydride in tetrahydrofuran.
McEwen, William E.,Grossi, Anthony V.,MacDonald, Russell J.,Stamegna, Andrew P.
p. 1301 - 1308
(2007/10/02)

A CONVENIENT ROUTE FOR THE PREPARATION OF AROMATIC ALDEHYDES
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Shankaran, K.,Rao, A.S.
p. 573 - 580
(2007/10/02)

Synthesis and antiinflammatory activity of 2,3-bis(p-methoxyphenyl)indole and related compounds.
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Szmuszkovicz,Glenn,Heinzelman,Hester Jr.,Youngdale
p. 527 - 536
(2007/10/04)