Aryl Carboxylic Acids Research Articles

Synthesis and CYP17α hydroxylase inhibition activity of new 3α- and 3β-ester derivatives of pregnenolone and related ether analogues

A new class of 3α-ester derivatives of pregnenolone, using Mitsunobu reaction conditions, is described. The scheme involved the conversion of pregnenolone (4) into 20-(2-hydroxyethyl)imino-pregn-5-en-3β-ol (8), followed by tritylation to give the analogue 9. Treatment of 9 with various aryl carboxylic acids afforded the tritylated 3α-ester pregnenolone analogues 18–23. Detritylation with AcOH furnished the 3α‐substituted aryl ester derivatives 24–29. Analogously, the 3β-ester analogues 31 and 32 were synthesized from pregnenolone (4) and its analogue 30, using Steglich coupling method, by treatment with rhodamine B in the presence of DCC/DMAP. These derivatives were screened for their CYP17α hydroxylase inhibition activity expressed in Escherichia coli. Compound 27 was the most active inhibitor among both series, with IC50 value of 1.12 μM and selectivity profile of 88.56 % inhibition of CYP17α hydroxylase enzyme.

ChemInform Abstract: Highly Chemoselective and Versatile Method for Direct Conversion of Carboxylic Acids to Ketones Utilizing Zinc Ate Complexes.

AbstractConditions for the efficient transformation of a broad range of aryl, hetaryl, alkyl, and alkenyl carboxylic acids into the corresponding methyl, ethyl, and butyl ketones are elaborated.

Palladium‐Catalyzed Carbonylations of Arylboronic Acids: Synthesis of Arylcarboxylic Acid Ethyl Esters

AbstractAn approach for the palladium‐catalyzed ethoxycarbonylations of arylboronic acids using diethyl pyrocarbonate as carbon monoxide/carbon dioxide (CO/CO2) surrogate in moderate to good yields has been investigated.magnified image

ChemInform Abstract: Synthesis and Selenation of Tandem Multicomponent Condensation Adducts.

AbstractSome four‐component condensation adducts are readily obtained by one‐pot reaction of aryl carboxylic acids, aryl aldehydes, arylamines, and c‐hexylisocyanide and treated with Woollins′ reagent leading to the formation of a series of new selenoamides.

Three-Dimensional Heterometallic Coordination Networks: Syntheses, Crystal Structures, Topologies, and Heterogeneous Catalysis

This work presents the synthesis of {Co3+-Zn2+} and {Co3+-Cd2+} heterometallic coordination networks. These networks are originated from two unique Co3+-based metalloligands containing appended arylcarboxylic acid groups at the strategically placed positions. Such appended arylcarboxylate groups coordinate the secondary metal ions, Zn2+ and Cd2+, to afford distinct three-dimensional networks. All four networks display orderly arrangement of secondary metal ions and unique network topologies including an unprecedented one. These networks have been shown to act as the heterogeneous and reusable catalysts for the Knoevenagel condensation reactions and cyanation reactions of assorted aldehydes. Cyanation reactions nicely demonstrate the substrate size-exclusion catalysis.

ChemInform Abstract: Direct Amide Synthesis from Equimolar Amounts of Carboxylic Acid and Amine Catalyzed by Mesoporous Silica SBA‐15.

AbstractThe heterogeneous amidation reaction proves successful for the transformation of aryl and alkyl carboxylic acids as well as N‐Boc‐protected amino acids with primary aliphatic amines and secondary amines such as morpholine while delivering the desired amides in high to excellent yields.

ChemInform Abstract: S‐Triazene Based Fluorous Coupling Reagent for Direct Amide Synthesis.

AbstractAlkyl, benzyl, aryl, and hetaryl carboxylic acids are successfully coupled with primary aliphatic and aromatic amines as well as secondary aliphatic amines.

Synthesis of Oxazolo[5,4‐d][1,2,4]triazolo[4,3‐a]pyrimidines as a New Class of Heterocyclic Compounds

Several new derivatives of oxazolo[5,4‐d]pyrimidine (3a, 3b, 3c, 3d, 3e, 3f, 3g, 3h) have been synthesized through the reaction of 2,4‐dichloro‐6‐methyl‐5‐nitropyrimidine (2) with aryl carboxylic acids in refluxing POCl3. Further treatment of compounds (3a, 3b, 3c, 3d, 3e, 3f, 3g, 3h) with hydrazine hydrate gave the hydrazine derivatives (4a, 4b, 4c, 4d, 4e, 4f, 4g, 4h) that were subsequently cyclized into a novel heterocyclic system, oxazolo[5,4‐d][1,2,4]triazolo[4,3‐a]pyrimidine (5a, 5b, 5c, 5d, 5e, 5f, 5g, 5h, 5i, 5j, 5k, 5l, 5m, 5n, 5o, 5p) and (7a, 7b, 7c, 7d) on treatment with triethylorthoesters or carbondisulfide and alkylhalides, respectively.

ChemInform Abstract: A Mild and Efficient Carboxylate‐Directed C—H Arylation of Aryl Carboxylic Acids with Iodobenzenes in Water.

AbstractThe Pd‐catalyzed reaction of carboxylic acids with iodobenzenes in water in the presence of the surfactant Tween 20 produces selectively ortho‐monoarylated products in good yield.

Rhodium(III)-Catalyzed [4+1] Annulation of Aromatic and Vinylic Carboxylic Acids with Allenes: An Efficient Method Towards Vinyl-Substituted Phthalides and 2-Furanones.

A highly regio- and stereoselective synthesis of 3,3-disubstituted phthalides from aryl carboxylic acids and allenes using a rhodium(III) catalyst has been demonstrated. The reaction features broad functional group tolerance and provides a simple and straightforward route to the synthesis of various 3-vinyl-substituted phthalides. Furthermore, the catalytic reaction can also be applied to the synthesis of biologically active 5-vinyl-substituted 2-furanones from α,β-unsaturated carboxylic acids and allenes. The reactions proceed through a carboxylate-assisted ortho-CH activation and [4+1] annulation. The preliminary mechanistic studies suggest that a CH cleavage is the rate-determining step.

ChemInform Abstract: Rh(III)‐Catalyzed Oxidative Coupling of Benzoic Acids with Geminal‐Substituted Vinyl Acetates: Synthesis of 3‐Substituted Isocoumarins.

AbstractBoth 3‐aryl and 3‐alkyl substituted isocoumarins are synthesized by a Rh(III)‐catalyzed C—H activation/annulation reaction of electron‐rich germinal‐substituted vinyl acetates and arylcarboxylic acids.

ChemInform Abstract: Rhodium‐Catalyzed Decarbonylative Direct C2‐Arylation of Indoles with Aryl Carboxylic Acids.

ChemInformVolume 46, Issue 16 Heterocyclic Compounds ChemInform Abstract: Rhodium-Catalyzed Decarbonylative Direct C2-Arylation of Indoles with Aryl Carboxylic Acids. Lingjuan Zhang, Lingjuan Zhang Dep. Chem., Renmin Univ., Beijing 100872, Peop. Rep. ChinaSearch for more papers by this authorXiao Xue, Xiao Xue Dep. Chem., Renmin Univ., Beijing 100872, Peop. Rep. ChinaSearch for more papers by this authorConghui Xu, Conghui Xu Dep. Chem., Renmin Univ., Beijing 100872, Peop. Rep. ChinaSearch for more papers by this authorYixiao Pan, Yixiao Pan Dep. Chem., Renmin Univ., Beijing 100872, Peop. Rep. ChinaSearch for more papers by this authorGuang Zhang, Guang Zhang Dep. Chem., Renmin Univ., Beijing 100872, Peop. Rep. ChinaSearch for more papers by this authorLijin Xu, Lijin Xu Dep. Chem., Renmin Univ., Beijing 100872, Peop. Rep. ChinaSearch for more papers by this authorHuanrong Li, Huanrong Li Dep. Chem., Renmin Univ., Beijing 100872, Peop. Rep. ChinaSearch for more papers by this authorZhangjie Shi, Zhangjie Shi Dep. Chem., Renmin Univ., Beijing 100872, Peop. Rep. ChinaSearch for more papers by this author Lingjuan Zhang, Lingjuan Zhang Dep. Chem., Renmin Univ., Beijing 100872, Peop. Rep. ChinaSearch for more papers by this authorXiao Xue, Xiao Xue Dep. Chem., Renmin Univ., Beijing 100872, Peop. Rep. ChinaSearch for more papers by this authorConghui Xu, Conghui Xu Dep. Chem., Renmin Univ., Beijing 100872, Peop. Rep. ChinaSearch for more papers by this authorYixiao Pan, Yixiao Pan Dep. Chem., Renmin Univ., Beijing 100872, Peop. Rep. ChinaSearch for more papers by this authorGuang Zhang, Guang Zhang Dep. Chem., Renmin Univ., Beijing 100872, Peop. Rep. ChinaSearch for more papers by this authorLijin Xu, Lijin Xu Dep. Chem., Renmin Univ., Beijing 100872, Peop. Rep. ChinaSearch for more papers by this authorHuanrong Li, Huanrong Li Dep. Chem., Renmin Univ., Beijing 100872, Peop. Rep. ChinaSearch for more papers by this authorZhangjie Shi, Zhangjie Shi Dep. Chem., Renmin Univ., Beijing 100872, Peop. Rep. ChinaSearch for more papers by this author First published: 02 April 2015 https://doi.org/10.1002/chin.201516157Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume46, Issue16April, 2015 RelatedInformation

ChemInform Abstract: Facile One‐Pot Synthesis of Benzimidazole and Quinoxalin‐2(1H)‐one Scaffolds via Two‐Component Coupling Reaction, Deprotection, and Intermolecular Cyclization.

AbstractVarious scaffolds of interest for medicinal chemistry are prepared by the reaction of alkyl, alkenyl, aryl, and hetaryl carboxylic acids or glyoxylic acids with 2‐(N‐Boc‐amino)phenylisocyanides.

ChemInform Abstract: Nickel‐Catalyzed Reductive Methylation of Alkyl Halides and Acid Chlorides with Methyl p‐Tosylate.

AbstractIn contrast to other sulfonates, methyl tosylate serves as an effective agent for the methylation of unactivated primary and secondary alkyl halides as well as aryl and alkyl carboxylic acid chlorides.

ChemInform Abstract: Transition‐Metal‐Free Hunsdiecker Reaction of Electron‐Rich Arenecarboxylic Acids and Aryl Aldehydes in Water.

AbstractDepending on the electron‐rich substituent of the aryl carboxylic acid or aldehyde used, either mono‐, di‐ or even trihalogenation may take place while preserving or substituting the aldehyde or carboxylic acid functionality, respectively.

Synthesis of Dibenzo[c,e]oxepin‐5(7H)‐ones from Benzyl Thioethers and Carboxylic Acids: Rhodium‐Catalyzed Double CH Activation Controlled by Different Directing Groups

AbstractA rhodium(III)‐catalyzed cross‐coupling of benzyl thioethers and aryl carboxylic acids through the two directing groups is reported. Useful structures with diverse substituents were efficiently synthesized in one step with the cleavage of four bonds (CH, CS, OH) and the formation of two bonds (CC, CO). The formed structure is the privileged core in natural products and bioactive molecules. This work highlights the power of using two different directing groups to enhance the selectivity of a double CH activation, the first of such examples in cross‐oxidative coupling.

Synthesis of dibenzo[c,e]oxepin-5(7H)-ones from benzyl thioethers and carboxylic acids: rhodium-catalyzed double C-H activation controlled by different directing groups.

A rhodium(III)-catalyzed cross-coupling of benzyl thioethers and aryl carboxylic acids through the two directing groups is reported. Useful structures with diverse substituents were efficiently synthesized in one step with the cleavage of four bonds (CH, CS, OH) and the formation of two bonds (CC, CO). The formed structure is the privileged core in natural products and bioactive molecules. This work highlights the power of using two different directing groups to enhance the selectivity of a double CH activation, the first of such examples in cross-oxidative coupling.

Metal‐Free, Room‐Temperature, Radical Alkoxycarbonylation of Aryldiazonium Salts through Visible‐Light Photoredox Catalysis

AbstractThe first radical alkoxycarboxylation of aryldiazonium salts using CO gas through visible‐light‐induced photoredox catalysis (16 W blue LEDs) has been developed. This reaction is entirely metal‐free, is carried out at room temperature with a low loading of an organic dye as a photocatalyst (0.5 mol %), and provides a wide range of arylcarboxylic acid esters in high yields. Importantly, this photocatalytic system can be successfully extended to other carboxylation reactions.

Synthesis and Selenation of Tandem Multicomponent Condensation Adducts

A number of four-component condensation adducts, which were readily obtained from one-pot reaction of aryl carboxylic acids, arylaldehydes, arylamines, and <i>c</i>-hexylisocyanide, were treated with two equivalents of Woollins’ reagent leading to the formation of a series of novel selenoamides with one or two C=Se groups or heterocyclic compounds such as 1,3-selenazole and 1,3-selenazolidin-5-one.

Carboxylic acids as traceless directing groups for the rhodium(III)-catalyzed decarboxylative C-H arylation of thiophenes.

A rhodium(III)-catalyzed carboxylic acid directed decarboxylative C-H/C-H cross-coupling of carboxylic acids with thiophenes has been developed. With a slight adjustment of the reaction conditions based on the nature of the substrates, aryl carboxylic acids with a variety of substituents could serve as suitable coupling partners, and a broad variety of functional groups were tolerated. This method provides straightforward access to biaryl scaffolds with diverse substitution patterns, many of which have conventionally been synthesized through lengthy synthetic sequences. An illustrative example is the one-step gram-scale synthesis of a biologically active 3,5-substituted 2-arylthiophene by way of the current method.