Multicomponent Reactions Of Amines Research Articles

Visible-Light-Driven Multicomponent Reactions for the Versatile Synthesis of Thioamides by Radical Thiocarbamoylation.

Thioamides are widely used structures in pharmaceuticals and agrochemicals, as well as important synthons for the construction of sulfur-containing heterocycles. This report presents a series of visible-light-driven multicomponent reactions of amines, carbon disulfide, and olefins for the mild and versatile synthesis of linear thioamides and cyclic thiolactams. The use of inexpensive and readily available carbon disulfide as the thiocarbonyl source in a radical pathway enables the facile assembly of structurally diverse amine moieties with non-nucleophilic carbon-based reaction partners. Radical thiocarbamoylative cyclization provides a practical protocol that complements traditional approaches to thiolactams relying on deoxythionation. Mechanistic studies reveal that direct photoexcitation of in situ formed dithiocarbamate anions as well as versatile photoinduced electron transfer with diverse electron acceptors are key to the reactions.

Visible‐Light‐Driven Multicomponent Reactions for the Versatile Synthesis of Thioamides by Radical Thiocarbamoylation

Thioamides are widely used structures in pharmaceuticals and agrochemicals, as well as important synthons for the construction of sulfur‐containing heterocycles. This report presents a series of visible‐light‐driven multicomponent reactions of amines, carbon disulfide, and olefins for the mild and versatile synthesis of linear thioamides and cyclic thiolactams. The use of inexpensive and readily available carbon disulfide as the thiocarbonyl source in a radical pathway enables the facile assembly of structurally diverse amine moieties with non‐nucleophilic carbon‐based reaction partners. Radical thiocarbamoylative cyclization provides a practical protocol that complements traditional approaches to thiolactams relying on deoxythionation. Mechanistic studies reveal that direct photoexcitation of in situ formed dithiocarbamate anions as well as versatile photoinduced electron transfer with diverse electron acceptors are key to the reactions.

Catalyst- and additive-free syntheses of rhodanine and S-alkyl dithiocarbamate derivatives from sulfoxonium ylides.

An efficient catalyst- and additive-free facile access to rhodanine and S-alkyl dithiocarbamate derivatives via multi-component reaction of amines, CS2 and α-ester sulfoxonium ylides in methanol has been described. The new synthetic methods offer excellent synthetic prospects for several functionalized rhodanines and S-alkyl dithiocarbamates with simple operational procedures.

Multicomponent Synthesis of Unsaturated γ-Lactam Derivatives. Applications as Antiproliferative Agents through the Bioisosterism Approach: Carbonyl vs. Phosphoryl Group.

We report efficient synthetic methodologies for the preparation of 3-amino and 3-hydroxy 3-pyrrolin-2-ones (unsaturated γ-lactams) through a multicomponent reaction of amines, aldehydes and acetylene or pyruvate derivatives. The densely substituted γ-lactam substrates show in vitro cytotoxicity, inhibiting the growth of the carcinoma human tumor cell lines RKO (human colon epithelial carcinoma), SKOV3 (human ovarian carcinoma) and A549 (carcinomic human alveolar basal epithelial cell). In view of the possibilities for the diversity of the substituents that offer a multicomponent, synthetic methodology, an extensive structure–activity profile is presented. In addition, the bioisosteric replacement of the flat ester group by a tetrahedral phosphonate or phosphine oxide moiety in γ-lactam substrates leads to increased growth inhibition activity. Cell morphology analysis and flow cytometry assays indicate that the main pathway by which our compounds induce cytotoxicity is based on the activation of the intracellular apoptotic mechanism.

A Multicomponent Protocol for the Synthesis of Highly Functionalized γ-Lactam Derivatives and Their Applications as Antiproliferative Agents.

An efficient synthetic methodology for the preparation of 3-amino 1,5-dihydro-2H-pyrrol-2-ones through a multicomponent reaction of amines, aldehydes, and pyruvate derivatives is reported. In addition, the densely substituted lactam substrates show in vitro cytotoxicity, inhibiting the growth of carcinoma human tumor cell lines HEK293 (human embryonic kidney), MCF7 (human breast adenocarcinoma), HTB81 (human prostate carcinoma), HeLa (human epithelioid cervix carcinoma), RKO (human colon epithelial carcinoma), SKOV3 (human ovarian carcinoma), and A549 (carcinomic human alveolar basal epithelial cell). Given the possibilities in the diversity of the substituents that offer the multicomponent synthetic methodology, an extensive structure-activity profile is presented. In addition, both enantiomers of phosphonate-derived γ-lactam have been synthesized and isolated and a study of the cytotoxic activity of the racemic substrate vs. its two enantiomers is also presented. Cell morphology analysis and flow cytometry assays indicate that the main pathway by which our compounds induce cytotoxicity is based on the activation of the intracellular apoptotic mechanism.

Multicomponent reaction of amine, carbon disulfide, and fluoronitrobenzene via nucleophilic attack on the fluorinated carbon for the synthesis of nitrophenyl methylcarbamodithioates

In this paper, multicomponent reaction of amine, carbon disulfide and fluoronitrobenzene is reported for the synthesis of nitrophenyl methylcarbamodithioate derivatives. The method is based on the nucleophilic attack of the activated methylcarbamodithioate salt to fluoronitrobenzene. Several starting materials are tested and successfully produced the corresponding nitrophenyl methylcarbamodithioate. A possible mechanism for the reaction is suggested.

ChemInform Abstract: Nano CoFe2O4 Supported Antimony(III) as an Efficient and Recyclable Catalyst for One‐Pot Three‐Component Synthesis of Multisubstituted Pyrroles.

AbstractThe title catalyst is successfully applied on the multicomponent reaction of amines, nitroolefin, and 1,3‐dicarbonyl compounds.

A simple and green approach for the synthesis of polyfunctionalized mono- and bis-dihydro-2-oxopyrroles catalyzed by trityl chloride

A simple synthesis of ployfunctionalized mono- and bis-dihydro-2-oxopyrrole derivatives is described by one-pot multi-component reaction of amines, dialkyl acetylenedicarboxylates and formaldehyde in the presence of trityl chloride (10 mol%) at room temperature in EtOH. The features of this procedure are mild and green reaction conditions, good to high yields, short reaction times, high atom economy, operational simplicity and no need for column chromatography.

Iron-doped single walled carbon nanotubes as an efficient and reusable heterogeneous catalyst for the synthesis of organophosphorus compounds under solvent-free conditions

Iron-doped single walled carbon nanotubes (Fe/SWCNTs) is an efficient, eco-friendly, and reusable heterogeneous catalyst for the synthesis of diversely decorated α-aminophosphonates via multicomponent reaction of amines, carbonyl compounds, and phosphorus compounds under solvent-free conditions. This methodology illustrates a very simple procedure, with wide applicability, extending the scope to aliphatic and aromatic amines and carbonyl compounds. It also enabled the development of one-pot synthesis of β-phosphonomalonates during the reaction of carbonyl compounds, malononitrile and phosphorus compounds. Excellent results were obtained in each case affording the corresponding organophosphorus adducts in good yields.

Multicomponent reactions of amines with aldehydes and H2S as efficient route to heterocycles and thioaza macrocycles

Here we provide new experimental results on multicomponent reactions of amines with aldehydes and H(2)S in the directed synthesis of functionally-substituted 1,3-thiazetidines, 1,3,5-dithiazinanes, 1,3,5-thiadiazinanes, 1,5-dithia-3,7-diazacyclooctanes, and thioaza macrocycles. X-ray analysis gave insight into the structure of the synthesized compounds. New kinds of multicomponent reactions (MCR) have been discovered and characterized.

Selective Formation of 2‐Imidazolines and 2‐Substituted Oxazoles by Using a Three‐Component Reaction

Selective formation of 2H-2-imidazolines and 2-substituted oxazoles by using a multicomponent reaction of amines, either aldehydes or ketones, and alpha-acidic isocyano amides or esters is described. By selecting the appropriate solvent, Ag(I) or Cu(I) catalyst, or by employing a weak Brønsted acid, the product formation can be fully controlled and directed quantitatively to the desired heterocyclic scaffold. The described experimental procedures not only significantly increase the scope of compatible inputs for this complexity-generating three-component reaction, but also allow for considerable chemical diversity: At least four diversity points in two distinct scaffolds can be exploited in this way.