Ruthenium(III) Chloride–Catalyzed Ring Opening of Epoxides with Aromatic Amines

Ruthenium(III) chloride catalyzes the nucleophilic opening of epoxides by anilines, leading to the efficient synthesis of β‐amino alcohols. High regioselectivity can be considered as a noteworthy advantage of this method.     

Aluminium Chloride–Catalyzed Synthesis of 4-Benzyl Cinnolines from Aryl Hydrazones

An efficient synthesis of 4-benzyl cinnolines from aryl phenylallylidene hydrazone is described. In this report aluminium chloride as a Lewis acid catalyst and toluene as a solvent are used for the synthesis. This method is expected to more advantageous than the other reported methods of synthesis of the cinnoline rings because of its low cost, better yield, and benign reaction conditions.

[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.]     

Silica Chloride–Catalyzed Synthesis of Thiiranes from Oxiranes Under Solvent-Free Conditions

A mild, simple, and efficient method for the synthesis of thiiranes from epoxides using a catalytic amount of silica chloride under solvent-free conditions has been developed. Experimental simplicity, simple work-up procedure, and solvent-free reaction conditions are important features of the present protocol.     

Benzylation of Aromatic Compounds with Benzyl Chloride Catalyzed by Nafion／Si02 Nanocomposite Catalyst

In the presence of Nafion/SiO2compounds with benzyl chloride proceedednanocomposite catalyst, the benzylation of aromatic to afford diphenylmethane derivatives in high yields,The catalyst showed high catalytic activity not only for electron-rich aromatic compounds, but also for electron-poor aromatic compounds. Under identical conditions, the self-benzylation of benzyl chloride, and dibenzylation and/or multi-benzylation of aromatic compounds were negligible     

Benzylation of Aromatic Compounds with Benzyl Chloride Catalyzed by Nafion/SiO_2 Nanocomposite Catalyst

Diphenylmethane and substituted diphenylmethane are important compounds forsynthesis chemistry as well as industrial chemistry. These compounds are easilysynthesized by the benzylation of aromatic compounds with benzyl chloride or benzylalcohol catalyzed by homogeneous acid catalysts, such as AlCl3, FeCl3, H2SO4, HF andBF3. However, these catalytic systems are highly corrosive, and usually proceed withlow selectivity. In addition, they are less satisfactory from the environmen…     

Magnesium Chloride–Catalyzed Thiolysis of Epoxides: Synthesis of β-hydroxy Sulfides

A mild and convenient ring opening of epoxides with thiophenol and its derivatives takes place at room temperature in the presence of magnesium chloride as catalyst to afford the corresponding β-hydroxy sulfides along with minor amounts of 2-chlorocycloalkanols in good yields. When the crude reaction mixtures are treated with aqueous sodium hydroxide solution, pure 2-arlythiocycloalkanols are obtained in good yields.     

Synthesis of Boron–Nitrogen–Phosphorus Compounds from N-Silylphosphoranimines

Two modes of reactivity of N-silylphosphoranimines have been utilized to prepare the title compounds containing either B–N=P or Si–N=P–N–B linkages. First, silicon-nitrogen bond cleavage reactions of the N-silylphosphoranimines, Me₃SiN=PMe(R)OCH₂CF₃ (1: R=Me, 2: R=Ph), with various chloroboranes gave the new N-borylphosphoranimines, Ph(Me₂N)B–N=PMe₂OCH₂CF₃ (2) and [(Me₃Si)₂N](Cl)B–N=PMe₂OCH₂CF₃ (10). In other cases, however, the expected B–N=P products were unstable and cyclic phosphazenes [Me(R)P=N]_3,4 were obtained. Second, deprotonation-substitution reactions of the aminophosphoranimines, Me₃SiN=P(R)Me–N(R)H, were used to prepare a series of novel (borylamino)-phosphoranimines, Me₃SiN=P(R)(Me)–N(R)–B(NMe₂)₂ (18: R=Me, R=t-Bu; 19: R=R=Me; 20: R=Ph, R=t-Bu; 21: R=Ph, R=Me) and Me₃SiN=PMe₂–N(t-Bu)–B(Ph)X (22: X=NMe₂, 23: X=OCH₂CF₃). All of the new boron–nitrogen–phosphorus products were fully characterized by multinuclear NMR (¹H, ¹³C, and ³¹P) spectroscopy and elemental analysis.     

Metal-Free Synthesis of Benzo[α]phenanthridines from Aromatic Aldehydes,Cyclohexanones,and Aromatic Amines

A three-component synthesis of benzo[α]phenanthridines from aromatic aldehydes,cyclohexanones,and aromatic amines has been developed,which is mediated by KI/DMS...     

Preparation of Aromatic Amines by Reduction of Aromatic Nitro Compounds with Metallic Tellurium in Near-Critical Water

Aromatic amines were prepared in good yields by a novel reduction of aromatic nitro compounds with tellurium metal in near-critical water at 275 ℃。     

Efficient Synthesis of β‐Amino Alcohols Catalyzed by Niobium Pentachloride: Regioselective Ring Opening of Epoxides with Aromatic Amines

Epoxides undergo a rapid ring‐opening reaction with aromatic amines catalyzed by niobium pentachloride under mild reaction conditions. All the reactions were carried out at room temperature to afford the corresponding β‐amino alcohols in excellent yields and with high regioselectivity.     

A Novel Synthesis of N-Methyl-N-aryl Carbamates from Aromatic Amines and Dimethyl Carbonate Catalyzed by K2CO3／Bu4NBr

A facile synthesis of N-methyl-N-aryl carbamates from aromatic amines and dimethyl carbonate (DMC) has been achieved with high yields in the presence of potassium carbonate (K2CO3) and tetrabutylammonium bromide (Bu4NBr) under solvent-free conditions.     

Iodine Catalyzed Three-component Strecker-type Synthesis of α-Aminonitriles from Aldehydes, Amines and Tributyltin Cyanide

A simple and efficient one-pot method has been developed for the synthesis of a-aminonitriles from aldehydes, amines and tributyltin cyanide in the presence of a catalytic amount of iodine with high yields. The reactions proceeded smoothly at room temperature via very simple procedure.     

CAN Catalyzed Preparation of β-Enamino Ketones from Amines and Acetylacetone

The enamino ketone moiety has attracted much interest because it is a basic and versatile structure for organic synthesis. A number of reviews have been published about the chemistry of β-enamino ketones1-3. It is therefore not surprising that many synth…     

Synthesis of Ipratropium Bromide–Related Compounds

Synthesis of ipratropium bromide metabolites is described.     

Alkali Metal–Promoted Facile Synthesis of Secondary Amines from Imines and Carbodiimides

We present here an efficient method for the hydroboration of aldimines (-C=N-) with pinacolborane (HBpin) using an alkali metal catalyst, potassium benzyl. The reaction was accomplished with unprecedented catalytic efficiency under mild and solvent-free conditions to afford the high yield of the corresponding N-boryl amines up to 97%. Various functionalities on aldimines were incorporated for hydroboration. The corresponding boryl amines were subjected to further hydrolysis to yield the corresponding secondary amines with good yields up to 89%. This protocol for the reaction demonstrates an atom-economic and green method with diverse imines that bears excellent functional group tolerance. Chemoselective reduction of imines was also attained, with good yields of 74–89%. We also propose the most plausible mechanism involving the formation of metal hydride as the active pre-catalyst.     

Ferric Chloride–Promoted Efficient and Facile BOC Protection of Amines

Amines are efficiently protected as their tertiary butyloxycarbonyl (BOC) derivatives under mild reaction condition when reacted with (BOC)₂O in the presence of FeCl₃. The present method is applicable to a variety of amines including aliphatic, aromatic, and hetero aromatic amines.     

Zirconium Catalyzed Hydroaminoalkylation for the Synthesis of α-Arylated Amines and N-Heterocycles

The zirconium catalyzed hydroaminoalkylation of alkenes with N-aryl- and sterically demanding N-alkyl-α-arylated secondary amines by using commercially available Zr(NMe₂)₄ is reported. N-phenyl- and N-isopropylbenzylamine are used as amine substrates to establish the alkene substrate scope. Exclusively linear products are obtained in the presence of bulky vinylsilanes. Challenging α-heteroarylated amines and functionalized alkene substrates are compatible with this easy to use catalyst, affording a new disconnection strategy for the atom- and step-economic preparation of selectively substituted saturated α-arylated heterocycles.     

Reactions of Aromatic Nitro Compounds: LXXIV. Azo Coupling of Anionic Nitroarene σ-Complexes with Aromatic Diazo Compounds. Effect of Reaction Conditions on the Yield of Nitroazobenzenes

Effect of a number of factors on the yield of nitroazobenzenes in the reaction of 4-nitro- and 4-dimethylaminobenzenediazonium tetrafluoroborates with anionic adducts derived from 1,3-dinitrobenzene was studied. Conditions were found which allow nitroazobenzenes to be prepared in 80-90% yield.     

Preparation of Sulphur-containing Aromatic Amines by Reduction of the Corresponding Aromatic Nitro Compounds with Hydrazine Hydrate over Iron Oxide Hydroxide Catalyst

The sulphur-containing aromatic amines are an important class of compounds frequently used as key intermediates in the synthesis of pharmaceutical products1,2, dyestuffs3-6 and polymers7. The usual methods for preparing sulphur-containing aromatic amines …     

p-Toluene Sulfonic Acid–Catalyzed,Solvent-Free Synthesis of Symmetrical Bisamides by Reaction Between Aldehydes and Amides

Reaction between aldehydes and amides catalyzed by p-toluene sulfonic acid in solvent-free conditions provided a simple and efficient one-pot route for the synthesis of symmetrical bisamide derivatives in excellent yields.