Advanced Routes in Synthesis and Reactions of Lawsone Molecules (2‐Hydroxynaphthalene‐1,4‐dione)

Lawsone (2‐hydroxynaphthalene‐1,4‐dione ) is a natural product which shows significant biological activity. Lawsone has been found as a component of many dyes as well as a constituent of medicinal herbal treatments. So, this review aimed to document the publications concerning the synthesis and chemical reactivity and reactions of lawsone reported by research groups.     

Microwave‐Assisted Three‐Component Synthesis of Some Novel 1‐Alkyl‐1H‐indole‐2,3‐dione 3‐(O‐Alkyl­oxime) Derivatives as Potential Chemotherapeutic Agents

A convenient and efficient method for a one‐pot conversion of N‐alkylisatins to N‐alkylisatin O‐alkyloximes 7a – 7n as potential chemotherapeutic agents is described (Scheme) (isatin=1H‐indole‐2,3‐dione). In this method, the microwave‐assisted three‐component reaction of N‐alkylisatins 8 , hydroxylamine hydrochloride, and diverse alkyl halides in the presence of K₂CO₃ and Bu₄NBr furnishes the corresponding N‐alkylisatin O‐alkyloximes under solvent‐free condition in short times (2–10 min) and good to excellent yields (62–83%). The O‐alkylation of in situ generated isatin oximes with alkyl halides was achieved regioselectively, and (Z)‐O‐alkyloximes were produced dominantly. PM3 Semi‐empirical quantum‐mechanic calculations were performed to rationalize the evidences, and the calculations indicated a lower heat of formation for the (Z)‐O‐alkyloximes.     

An Efficient Synthesis of Spiro‐oxindole Derivatives by Three‐Component Reactions in Water

An efficient synthesis of (3S)‐1,1′,2,2′,3′,4′,6′,7′‐octahydro‐9′‐nitro‐2,6′‐dioxospiro[3H‐indole‐3,8′‐[8H]pyrido[1,2‐a]pyrimidine]‐7′‐carbonitrile is achieved via a three‐component reaction of isatin, ethyl cyanoacetate, and 1,2,3,4,5,6‐hexahydro‐2‐(nitromethylidene)pyrimidine. The present method does not involve any hazardous organic solvents or catalysts. Also the synthesis of ethyl 6′‐amino‐1,1′,2,2′,3′,4′‐hexahydro‐9′‐nitro‐2‐oxospiro[3H‐indole‐3,8′‐[8H]pyrido[1,2‐a]pyrimidine]‐7′‐carboxylates in high yields, at reflux, using a catalytic amount of piperidine, is described. The structures were confirmed spectroscopically (IR, ¹H‐ and ¹³C‐NMR, and EI‐MS data) and by elemental analyses. A plausible mechanism for this reaction is proposed (Scheme 2).     

Facile Synthesis of 3‐Substituted Isoquinolines Derivatives via Microwave‐assisted Tandem Three‐component Coupling Cyclization

A novel three‐component reaction of o‐bromobenzaldehyde, terminal alkynes and tert‐butyl amine has been established, which proceeded smoothly to give 3‐substituted isoquinolines in good yields in the presence of palladium/copper catalysts under microwave irradiation.     

Microwave‐Assisted Three‐Component Reactions Leading to Pyrano‐Fused Pyrazolo[3,4‐b]pyridines

A series of pyrano‐fused pyrazolo[3,4‐b]pyridine derivatives with an aryl group presenting the 2‐position of the pyridine nucleus have been synthesized by microwave‐assisted three‐component reactions of aldehydes, tetrahydropyran‐4‐one, and 3‐methyl‐1‐phenyl‐1H‐pyrazol‐5‐amine in HOAc. This method is very efficient because of short reaction times and easy work‐up, and it provides an efficient and promising synthetic strategy for the construction of the tricyclic pyrano‐fused pyrazolo[3,4‐b]pyridine skeleton.     

A New Approach to the Synthesis of Poly‐Functionalized Pyrano[2,3‐d]Pyrimidines Derivatives via Microwave‐Assisted Multi‐Component Reactions without Catalyst

A facile microwave‐assisted synthesis of pyrano[2,3‐d]pyrimidines derivatives is accomplished via reactions of 4‐arylmethylene‐2‐phenyloxazol‐5(4H)‐ones with pyrimidine‐4,6‐diol in ethylene glycol. The reaction is simple to perform and occurs under mild conditions with broad scope of applicability.     

Asymmetric Synthesis of Heterocyclic γ‐Amino‐Acid and Diamine Derivatives by Three‐Component Radical Cascade Reactions

An enantioselective three‐component radical reaction of quinolines or pyridines with enamides and α‐bromo carbonyl compounds by dual photoredox and chiral Brønsted acid catalysis is presented. A range of valuable chiral γ‐amino‐acid derivatives are accessible in high chemo‐, regio‐, and enantioselectivity from simple, readily available starting materials under mild reaction conditions. Using the same strategy, the asymmetric synthesis of 1,2‐diamine derivatives is also reported.     

One‐Pot Three‐Component Synthesis of Oxazine Derivatives in Water

A one‐pot synthesis of oxazine derivatives via reaction between activated acetylenic compounds, benzoyl cyanide, and N‐nucleophiles in water as the solvent is described?.     

Synthesis of Spiro Pyrrolobenzothiazole Derivatives via a Three‐Component Reaction

A novel three‐component reaction involving 2‐methylbenzothiazole or 2,5‐dimethylbenzothiazole, acetylenic esters and 1,3‐dicarbonyl compounds such as (1,3‐dimethylbarbituric acid or 1,3‐indanedione) leading to the synthesis of spiro pyrrolobenzothiazole derivatives. The reactions proceeded smoothly at room temperature without using any catalyst. This method is very useful to functionalize benzothiazole derivatives in a one‐pot operation. The structures of the synthesized compounds have been characterized by spectral studies.     

Rapid and Efficient Microwave‐Assisted Synthesis of Some New Triazol‐3‐one Derivatives

A growing body of literature has shown the effectiveness of using microwaves in chemical reactions. The aim of this study is to demonstrate a rapid and highly efficient synthesis of some new triazol‐3‐ones via microwave heating using a monomode microwave. Compared with the thermal process, the microwave heating induces a dramatic reduction of the reaction time and improvement of the yields. In this study, rapid N‐benzylation and N‐acetylation of triazol‐3‐ones were achieved by microwave irradiation method for the first time. The newly synthesized compounds showed moderate antimicrobial activity against the standard bacterial and fungal organisms tested.     

Synthesis of Chromene Derivatives via Three‐Component Reaction of 4‐hydroxycumarin Catalyzed by Magnetic Fe3O4 Nanoparticles in Water

An easy and effective procedure for one‐pot three components coupling of 4‐hydroxycumarin, isothiocyanates, and isocyanides in water by employing magnetically recoverable Fe₃O₄ nanoparticles is described. Variety of chromene were produced a derivatives in high yields by using of this procedure. The catalyst can be recovered and recycled without a considerable decrease in the catalytic activity.     

An Efficient Synthesis of New Dispiropyrrolidine Derivatives via Three‐Component 1,3‐Dipolar Cycloaddition Reaction

A series of new dispiropyrrolidine derivatives were synthesized via the three‐component 1,3‐dipolar cycloaddition reaction of azomethine ylides generated in situ by the decarboxylative condensation of acenaphthenequinone and sarcosine or l ‐thioproline with 5‐benzylidene‐1,3‐dimethylpyrimidine‐2,4,6‐trione. The structures of the products were identified by IR, ¹H‐NMR, and HRMS spectra.     

Catalyst‐Free Reaction in Water: Synthesis of Functionalized Tetrahydroindole Derivatives via Three‐Component Domino Reaction

An environmentally benign and efficient method has been developed for the synthesis of functionalized tetrahydroindole derivatives in aqueous media under catalyst‐free conditions, by simply combining a phenylglyoxal monohydrate, an enaminone, and a barbituric acid. The advantages of this method are that it is catalyst free, has an easy workup, provides good yields, and uses water as solvent, which make this procedure facile and practical.     

Synthesis of 2‐Arylbenzothiazoles by Copper‐Catalyzed One‐Pot Three‐Component Reactions in Water

Copper‐catalyzed three‐component reactions of 2‐iodoanilines, benzylamines, and sulfur powder are reported to afford benzothiazoles in a simple one‐pot procedure by using water as solvent. A variety of 2‐arylbenzothiazoles were obtained in moderate to good yields up to 88%.     

One‐Pot Microwave‐Assisted Synthesis of Benzopyrano[2,3‐c]pyrazol‐3‐one Derivatives

A convenient one‐pot microwave‐assisted synthesis of Benzopyrano[2,3‐c]pyrazol‐3‐one derivatives was developed, where Knoevenagel condensation and hydrazinolysis reactions were continuously performed under microwave irradiation without separation and purification of the intermediates until the last cyclocondensation reaction except the substrates addition. The one‐pot procedure exhibited shorter reaction times and higher yields (25–55%) of the objects than the conventional heating method.     

Microwave‐Assisted Rapid Synthesis of Novel 1,5‐Benzodiazepine Derivatives as Potent Antimicrobial Agent

A new series of highly functionalized 1,5‐benzodiazepine derivatives 5a–x have been synthesized from 3‐[(1E)‐N‐(2‐aminophenyl) ethanimidoyl]‐4‐hydroxyl‐2H‐chromen‐2‐one 3a–c and pyrazole aldehyde 4a–h using catalytic amount of triflouro acetic acid under microwave irradiation. The main significant of the present procedure is shorter reaction time, easy work up procedure, and excellent yield with high purity. The structures of all the compounds were established on the basis of their IR, NMR, and mass spectral data and have been screened for their antimicrobial activity and antifungal activity.     

An Efficient Three‐Component Synthesis of Pyranoquinoline Derivatives

Pyranoquinoline derivatives have been synthesized via three‐component reaction of 4‐hydroxy‐1‐methyl‐2(1H)‐quinolinone and dialkyl acetylenedicarboxylates in the presence of nucleophiles such as alkyl isocyanides and triphenylphosphine.