Efficient Domino Reaction Research Articles

A facile potassium 18-crown ether catalysed synthesis of 2,6-dicyanoaniline and 3-amino-9,10-dihydrophenanthrene-2,4 dicarbonitrile and their in vitro intercalation study on calf thymus DNA

An efficient two-component domino reaction strategy has been developed for the synthesis of 2,6-dicyanoaniline and 3-amino-9,10-dihydrophenanthrene-2,4-dicarbonitrile derivatives in moderate to good yield by the reaction between malononitrile and β-chloro-α,β-unsaturated aldehydes catalyzed by potassium hydroxide-18-crown-6 in methanol. In-vitro intercalation studies of 3-amino-9,10-dihydrophenanthrene-2,4-dicarbonitriles with Calf-Thymus DNA have been carried out which reveal that the moiety interacts with an affinity greater than that of ethidium bromide (EtBr).

Nickel‐Catalyzed Synthesis of N‐(Hetero)aryl Carbamates from Cyanate Salts and Phenols Activated with Cyanuric Chloride

AbstractA simple and efficient domino reaction has been designed and employed for the one‐pot synthesis of N‐(hetero)aryl carbamates through the reaction between alcohols and in‐situ produced (hetero)aryl isocyanates in the presence of a nickel catalyst. The phenolic C−O bond was activated via the reaction of phenol with cyanuric chloride (2,4,6‐trichloro‐1,3,5‐triazine (TCT)) as an inexpensive and readily available reagent. This strategy provides practical access to N‐(hetero)aryl carbamates in good yields with high functional groups compatibility.

Synthesis of 1,2-Dihydro-Substituted Aniline Analogues Involving N-Phenyl-3-aza-Cope Rearrangement Using a Metal-Free Catalytic Approach

An efficient metal-free domino reaction leading to structural/electronically divergent 1,2-dihydropyridines from easily accessible propargyl vinyl anilines via N-phenyl 3-aza-Cope sigmatropic rearrangement is reported with good to excellent yields using 1,2-dichlorobenzene as solvent under thermal conditions. Spirocyclic substitution is also tolerated under the present optimized conditions.

Domino reactions of vinyl ethynyl ketones with 1-aryl-3,4-dihydroisoquinolines — Search for selectivity

We report an efficient domino reaction for synthesizing new pyrrolo[2,1-a]isoquinolines from 1-aryl-3,4-dihydroisoquinolines and vinyl ethynyl ketones. We also address the chemical selectivity of vinyl ethynyl ketones; i.e., adduct formation by the double or triple bond. The reaction outcome depends on the solvent, temperature, microwave irradiation, and catalyst. Donor substituents in the initial isoquinolines provide a regioselective addition to double or triple bonds.

A domino reaction of 3-chlorochromones with aminoheterocycles. Synthesis of pyrazolopyridines and benzofuropyridines and their optical and ecto-5'-nucleotidase inhibitory effects.

A new and efficient domino reaction of 3-chlorochromones with electron-rich aminoheterocycles was developed which allows for a convenient synthesis of a variety of pyrazolo[3,4-b]pyridines, pyrrolo[2,3-b]pyridines, pyrido[2,3-d]pyrimidines and benzofuro[3,2-b]pyridines. The products exhibit strong fluorescence. In addition, they exhibit significant ecto-5'-nucleotidase inhibition properties and cytotoxic behavior.

TSA-catalyzed regioselective synthesis of medicinally important 4-aryl-substituted dihydropyrimidine derivatives fused to pyrazole and triazole scaffolds via an efficient and green Domino reaction

A novel class of medicinally important 4-aryl-substituted dihydropyrimidine derivatives fused to pyrazole and triazole scaffolds has been found which is obtained via a newly designed regioselective domino reaction using tungstate sulfuric acid (TSA) as a Bronsted acid recyclable catalyst. Throughout this tri-component tandem reaction, 4-aryl-substituted dihydropyrimidine derivatives fused to pyrazole and triazole moieties were regioselectively formed under environmentally benign solvent-free conditions with high yields. By this achievement, some novel potentially interesting biologically active products were synthesized via a green and eco-friendly procedure.

One‐Pot Synthesis of 7‐chloro‐2‐arylthieno[3,2‐b]pyridin‐3‐ols and Their Derivatization to the Corresponding Arylamino, Arylthio, and Aryloxy Derivatives

A simple and efficient domino reaction for synthesis of 7‐chloro‐2‐arylthieno[3,2‐b]pyridin‐3‐ols (3) followed by derivatization into their corresponding aminoaryl (7a–7j), aryloxy (9a–9c), and thioaryloxy derivatives (8a–8k)is presented. The synthesis includes thioalkylation on 3‐position of methyl 4‐chloropicolinate (1) followed by in situ cyclization to give 7‐chloro‐2‐arylthieno[3,2‐b]pyridin‐3‐ols (3). The substitution of the chloro group with amines, phenols and thiophenols afforded the corresponding derivatives.

Domino Synthesis of Thiochromenes through Cu-Catalyzed Incorporation of Sulfur Using Xanthate Surrogate.

An efficient domino reaction has been developed for the synthesis of thiochromenes through Cu-catalyzed in situ incorporation of sulfur. This domino method avoids the use of less accessible and unpleasant arenethiols as starting materials, instead utilizes very stable aryl halides along with potassium ethyl xanthate as an odorless sulfur surrogate. The domino methodology proceeds through C(aryl)-S coupling, thioester cleavage, sulfa-Michael addition, aldol reaction, and elimination reaction sequences to provide thiochromenes in good yields.

Iron-Mediated Domino Interrupted Iso-Nazarov/Dearomative (3 + 2)-Cycloaddition of Electrophilic Indoles.

An efficient domino reaction combining different classes of pericyclic reactions leads to chiral complex polycyclic indoline-based architectures from achiral starting materials under mild conditions. This practical method is based on the ability of iron(III) chloride to promote both 4π electrocyclizations of 2,4-dienals and the C2-C3 umpolung of N-acetylindoles during the dearomative (3 + 2) cycloadditions.

ChemInform Abstract: Metal‐Free Three‐Component Domino Approach to Phosphonylated Triazolines and Triazoles.

AbstractThe efficient domino reaction between aryl, hetaryl or alkyl aldehydes, including benzodicarbaldehydes, aliphatic amines and the Bestmann‐Ohira reagents provides 1,4,5‐trisubstituted 1,2,3‐triazolines.

Gold-catalyzed formation of C–O and C–C bonds: An efficient domino reaction synthesis of functionalized furans

An efficient gold-catalyzed domino reaction for the synthesis of furan derivatives from haloalkynes has been described. This transformation has provided a new route for the formation of C–O and C–C bonds that prepare functionalized furans.

Correction to Phototriggered Base Proliferation: A Highly Efficient Domino Reaction for Creating Functionally Photo-Screened Materials

Correction to Phototriggered Base Proliferation: A Highly Efficient Domino Reaction for Creating Functionally Photo-Screened Materials

ChemInform Abstract: Synthesis of Chiral 1,2‐Dihydronaphtho[2,1‐b]furans by Organocatalytic Domino Reactions Catalyzed with Multiple Catalysis.

A chiral multiple catalysis with two chiral units has been proved effective in the domino Friedel–Crafts alkylation of β-naphthols with α-bromonitroalkenes. This novel and efficient domino reaction affords chiral 1,2-dihydronaphtho[2,1-b]furans in good to high yields and enantioselectivities (up to 93 % yield, 91 % enantiomeric excess).

Base‐Catalyzed Domino Michael–Alkylation–Rearrangement Reaction: A Synthetic Route to Functionalized 2,3‐Dihydrofurans

AbstractAn unexpected and efficient domino reaction of N‐sulfonyl‐1‐aza‐1,3‐dienes with 2‐halo‐1,3‐dicarbonyl compounds to synthesize differently substituted 2,3‐dihydrofuran derivatives with excellent regio‐, chemo‐, and stereoselectivity in moderate to good yields was developed. In this transformation, broad substrate scope was demonstrated, and a plausible mechanism for this novel domino reaction was given.

ChemInform Abstract: Ultrasound‐Promoted Efficient Domino Reaction for the One‐Pot Synthesis of Spiro‐5‐cyanopyrimidines: A Rapid Procedure.

AbstractThe three‐component one‐pot synthesis of the title compounds gives considerably higher yields with shorter reaction times when conducted under ultrasonic irradiation compared to conventional heating.

A Facile Synthesis and Anticancer Activity Evaluation of Spiro Analogues of Benzothiazolylchromeno/pyrano Derivatives

The spiro analogues of benzothiazolylchromenopyranopyridine, benzothiazolyl- chromenoquinoline, benzothiazolylpyranoquinoline, benzothiazolylchromenopyridopyrimidine and benzothiazolylpyranopyridopyrimidine have been synthesized by an efficient domino reaction using sulfamic acid as catalyst in aqueous medium and screened for their cytotoxic activity against tumor cell lines, namely human cancer cell lines of colon (sw620), breast (MCF-7), cervix (HeLa) and heptatoma (HepG2) using a sulforhodamine B (SRB) assay. The synthesized compounds have shown promising cytotoxic activity against MCF-7 (breast cancer) & HeLa (cervical cancer) cancer cell lines. Keywords: Multicomponent reactions, Spiroheterocycles, Cytotoxic activity, SRB assay, 2-aminobenzothiazole, Water.

Phototriggered Base Proliferation: A Highly Efficient Domino Reaction for Creating Functionally Photo-Screened Materials

Phototriggered base proliferation as a highly efficient domino reaction is presented for creating functionally photo-screened materials, providing a strategy for the photopolymerization of shadow areas via chemically diffuse amines toward the nonirradiated areas during polymerization. By integrating proliferated amines with a peroxide initiator (dibenzoyl peroxide, BPO), phototriggered self-propagating polymerization of acrylate monomers in three-dimensional space was achieved. The advantages of this approach lie in its enhanced photosensitivity, increased propagating velocity, and elevated double-bond conversion (90%) while reducing the local high temperature and the minimum BPO concentration that sustain a traveling front. Astonishingly, the propagating velocity and local maximum temperature can be well-modulated by varied BPO concentration and the appropriate amount of BA-BPD (1-(9-fluorenylmethoxycarbonyl)-4-benzylpiperidine) concentration, respectively. Finally, functionally photo-screened material containing carbon nanotubes was successfully prepared by phototriggered base proliferation reactions.

Ultrasound-promoted efficient domino reaction for the one-pot synthesis of spiro-5-cyanopyrimidines: a rapid procedure

A novel and efficient protocol has been developed for the synthesis of various spiro-5-cyanopyrimidines via the three-component condensation of cyclic ketones, nitrile derivatives, and thiourea or urea in ethanol at 60 °C using K2CO3 as catalyst under ultrasonic irradiation. In comparison to conventional methods, high yields, easy work-up, and short reaction times are advantages of this sonocatalyzed procedure. The effects of the catalyst, solvent, and temperature were examined. .

Toward the synthesis of 6-hydroxyquinoline starting from glycerol via improved microwave-assisted modified Skraup reaction

An efficient and modified Skraup reaction and Bamberger rearrangement in neat water were developed using nitrobenzene and an inexpensive, abundant and environmentally-friendly glycerol under microwave irradiation conditions was furnish regioselectively to the 6-hydroxyquinoline. The target compound was obtained in 77% yield via efficient domino reaction with a “one pot eleven steps”.

ChemInform Abstract: An Efficient Domino Reaction in Ionic Liquid: Synthesis and Biological Evaluation of Some Pyrano‐ and Thiopyrano‐Fused Heterocycles.

AbstractA series of pyrazolopyran annulated‐pyrano‐fused coumarins (V) and thiopyrano‐fused quinolones (III) are obtained in an improved domino/Knoevenagel‐hetero‐Diels—Alder reaction of aldehydes (I) and (IV) with pyrazolones (II).