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A versatile route to 1,2,5-trisubstituded γ-lactams with tertiary alcohol functionality at the 3-position, from homoallylic amine derivatives with a methyl group at the β-position, is presented.

The method serves for the efficient preparation of highly functionalized 3-substituted 2-quinolinones as well as 2,3-disubstituted quinolines.

The title acetoacetamides are obtained from various amine derivatives and dioxin-4-one by conventional and microwave-assisted heating.

Conditions for the ortho-selective trimethylsilylation of oxalyl amide protected benzylamine and phenylethylamine derivatives are developed which tolerate a diverse range of functional groups.

Solvent-free synthesis of 3-substituted indole derivatives by a one-pot three-component coupling reaction between aldehyde, N-alkyl aniline and indole by Fe(HSO4)3 catalyzed is described. The noticeable features of this protocol are the simplicity of the procedure, easy synthesized, recyclable and inexpensive catalyst, no organic solvent and high yields in relatively short reaction times.

The title compounds are efficiently obtained by reaction of 2-phenylquinazolin-4-amine with various aromatic aldehydes and isocyanides under solvent-free and environmentally benign conditions.

Allylboronic acids directly react with acyl hydrazones, affording homoallylic amine derivatives. The reaction proceeds with very high syn selectivity, which is the opposite of the stereochemistry observed for allylboration of imines. The reaction can be carried out with both aromatic and aliphatic acyl hydrazones. Based on our studies the excellent syn stereochemistry can be explained by chelation control of the acyl hydrazone and the B(OH)2 moiety.

We report a simple and efficient method for the synthesis of triarylamine derivatives using copper iodide nanoparticles, 1,10-phenanthroline and potassium hydroxide. Copper iodide nanoparticles enhanced the rate and ease of reaction and exhibited a high influence in the efficient synthesis of various amine derivatives. The nanoparticles also increased the yields of products and decreased the reaction times in all cases. The heterogeneous mediator was fully characterized by scanning electron microscopy and X-ray diffraction techniques.

1-Substituted 3-[3-methyl-1H-pyrazol-5-yl]thioureas react with ω-bromoacetophenones forming N-substituted(thiazol-2-ylidene)pyrazol-5-amine derivatives. Rational for these conversations are presented.

A green protocol for the synthesis of 2-aminoquinoxaline derivatives and related compounds via CeO2-catalyzed three-component reaction between 1,2-diamines, carbonyl compounds, and isocyanides is presented.

Tryptamine- and phenethylamine-derived imides were selectively monotrifluoromethylated using CF3TMS. Subsequent methanesulfonic acid mediated cyclization of the intermediate hemiaminals afforded the α-trifluoromethylated amine derivatives via the formation of trifluoromethylated acyliminium ions, in one pot. The strategy was applicable to the both inter- and intramolecular versions. Furthermore, the utility of the present method was demonstrated through the synthesis of trifluoromethylated analogues of harmicine and crispine A.

The title reaction occurs by a tandem 6-endo-cyclization, nucleophilic addition, 5-endo-cyclization and aromatization, providing cycloadducts in moderate to good yields with exclusive regioselectivity.

Various aldehydes and ketones were efficiently transformed into the corresponding amines using amine derivatives in the presence of triethylsilane and a catalytic amount of palladium on activated carbon in ethanol. The proposed method provides a one-pot synthesis of various amines in excellent yields after short reaction times. Copyright © 2013 John Wiley & Sons, Ltd.

The diastereoselective addition of an allylic indium intermediate to chiral o-bromophenyl sulfinyl imine 4 proceeded with good levels of diastereoselectivity. The resulting homoallylic amine derivatives were transformed into lactams 7 and 12, which upon copper-mediated intramolecular N-arylation led to the formation of benzo-fused 1-azabicyclo[j.k.0]alkanes 8 and 13. Benzo-fused 2-allyl-substituted heterocycles 14 could also be prepared by means of a palladium-catalyzed N-arylation of the corresponding free amines. The synthesis of the alkaloid (−)-angustureine was easily accomplished from (S)-2-allyltetrahydroquinoline (14b).

The direct oxidative conversion of simple, nonactivated alkenes into allylic amine derivatives represents a profound challenge to contemporary chemical synthesis. This article provides an overview on recent methodological developments and applications in the realm of modern palladium- and selenium-catalyzed oxidative allylic amination reactions.

Nucleophilic addition to carbon–nitrogen double bonds (imines) represents one of the most common strategies for the synthesis of amine derivatives. In order to circumvent the problem associated with low reactivity of imines in nucleophilic addition, various imines with electron-withdrawing groups at nitrogen have been studied, and many of them were successfully applied in asymmetric methodologies. Especially N-carbamoyl imines were found to be useful in the enantioselective synthesis of various organic compounds, due to their increased reactivity toward nucleophiles as well as limited difficulties connected with the removal of the carbamoyl moiety in target molecules. The aim of this review is to cover enantioselective methods based on N-carbamoyl imines, focusing on synthetically useful protocols.

Catalytic amounts of the Lewis acid B(C6 F5 )3 enable the hydroamination of terminal alkynes by aryl amines to the corresponding enamines. In accord with the results of stoichiometric reactions, the mechanism of this reaction involves a frustrated Lewis pair (FLP). The hydroamination can be followed by an FLP-catalyzed hydrogenation, resulting in a one-pot stepwise synthesis of amine derivatives.

The term ‘super base’ is generally applied to ionic metal-containing bases that undergo irreversible proton abstraction. However, non-ionic powerful amine derivatives of amidines, guanidines, phosphazenes, and Verkade’s bases with comparable or higher basicity to that of 1,8-bis(dimethylamino)naphthalene can all be arbitrarily classified as organic superbases. This Cluster contains manuscripts that present recent progress on organic superbases, including their applications in organic synthesis but, before proceeding, let us consider what class of molecule constitutes an organic superbase.

A synthetically versatile protocol for the stereospecific cyclization of homoallyl amine derivatives (I) to deliver cis-azetidines (III) and cis- or trans-pyrrolidine derivatives (V)—(IX) is developed.

A thiamine hydrochloride catalyzed three-component one-pot synthesis of the title compounds is described.

A new method for the conversion of alcohols to amine derivatives under retention of the configuration is reported.

Novel imidazo[2,1-b]thiazol-5-amine derivatives were synthesized by a one-pot, four-component reaction of 2-bromoacetophenone derivatives, aromatic aldehydes, thiourea, and isocyanides in the presence of ammonium chloride (NH4Cl) in toluene under reflux conditions. Moderate to good yields resulted and the reaction showed tolerance toward a range of aromatic aldehydes with electron-donating and electron-withdrawing substituents on either­ para or ortho positions.

The rearrangement of fluorinated allylic trichloroacetimidates produces the target compounds with excellent regio- and stereoselectivity.

The methodology has the advantages of operational simplicity, high efficiency, low costs and mild reaction conditions.

A new approach for the preparation of new 9-(alkyl or aryl)acenaphtho[1,2-b]furan-8-(alky or aryl) amine derivatives has been reported by the catalyst-free one-pot cyclocondensation of (acenaphthylen-1-yloxy)trimethylsilane, alkyl and aryl aldehydes, and aryl and alky isocyanides in refluxing DMF.

Mono N-Boc protection of various amines succeeds chemoselectively in the presence of magnetically recoverable ferric oxide on silica nanoparticles.

Title compounds (III) are obtained by a Friedlaender-type reaction using excess cycloalkanone (2 to 4 equiv.).

The optimized conditions are applied to the preparation of 20 derivatives of pharmaceutical interest.

The stereoselective formation of C–O, C–S and C–N bonds by the reaction of phenols, thiols and amines with activated alkynes is described. The reactions are successfully conducted in water with excellent yields at room temperature. The lack of organic solvent use in the work-up procedure, the short reaction time and the environmentally benign mild reaction conditions are advantages of this method.

Palladium-catalyzed hydroalkylation of allylic amines with alkylzinc reagents proceeds with high to excellent chemoselectivity in favor of anti-Markovnikov products in most cases (linear-to-branched ratio from 8:1 up to

The procedure allows the preparation of polysubstituted pyrazine derivatives of pharmaceutical interest within a short time.

A variety of synthetically valuable multifunctional homopropargyl amine derivatives is prepared via reaction of dihydropyridone triflates with BuLi.

Three-component condensation of o-phenylenediamine (I) with aliphatic or alicyclic ketones (II), (V) and isonitriles (III) proceeds efficiently in the presence of catalytic amounts of EDTA in water to give title dihydroquinoxalinamines (IV) and (VI) in high yields.

Carbamic acid 2-trimethylsilylethyl ester (Teoc-NH 2 ) serves as an ammonia equivalent in the palladium-catalyzed amination of aryl bromides and aryl chlorides. Anilines with sensitive functional groups can be readily prepared using these amine derivatives.

The reaction of trans-γ-aminoenones, generated from allylic amine derivatives and enones, under acidic or Heck arylation conditions lead to a variety of mono-, di- and trisubstituted pyrroles.

Twentyfour oxazinocarbazoles (IV) are prepared by a Mannich type condensation of N-substituted hydroxycarbazoles (I) with formaldehyde (II) and primary amines (III).

Title reaction with cyclic enamines affords chiral 2,2,2-trichloroethyl amine derivatives with high diastereo- and enantioselectivity.

The transformation of enaminochlorovinyl ketone 2 via the diketone 3 into a mixture of keto–enol tautomers 4 and 5 , synthons for 13-azaprostanoids, is described; reactions of compound 1 with amine derivatives of different types leading to abnormal products have also been studied.

The dimethyldioxirane oxidations of allenic amine derivatives give highly functionalized nitrogen heterocycles derived from cyclizations of intermediate allene mono- and diepoxides.

Aryl groups were introduced into the position β to the nitrogen atom of cyclic amines by carrying out the anodic α-methoxylation of cyclic amine derivatives, the elimination of methanol from the oxidized products, the halomethoxylation of the resulting α,β-unsaturated cyclic amine derivatives, the replacement of the α-methoxy group with an aryl group, and the silver ion-promoted migration of the α-aryl group to the β-position, consecutively. This method was applied to the synthesis of some alkaloids such as (±)-mesembrine.

N-benzyl-3,11-azatricyclo[6.3.0.0]undecane and N-octyl-3,11-azatricyclo[6.3.0.0]undecane, two triquinane compounds containing an endocyclic nitrogen atom and differing side-chains, were synthesized by thermal 2 + 2 cycloreversion from the symmetric cage compound pentacyclo[5.4.0.0.0.0]undecane-8,11-dione. The conformation of the cyclic system showed close similarity with the conformation of the hydrate of 4-methyltricyclo[6.3.0.0]undeca-3,11-dione. Both N-benzyl-3,11-azatricyclo[6.3.0.0]undecane and N-octyl-3,11-azatricyclo[6.3.0.0]undecane showed similar suppressant activity on the Ca2+ action potential of guinea-pig papillary muscle--the benzyl (aromatic) derivative fully suppressed the action potential (AP) whilst the aliphatic (octyl) derivative suppressed the AP to about 50% at the same dosages. Similarly, both these compounds (irreversibly) suppressed the chronotropy of spontaneously contracting guinea-pig atria by approximately 30% at concentrations of 1 x 10(-5) M or more.