Catalyzed Domino Reaction Research Articles

ChemInform Abstract: Convenient Synthesis of Substituted Tetrahydrofuran via Lewis Base Catalyzed [3 + 2] Domino Reactions.

A DABCO catalyzed domino reaction between 3-oxo-4-(2-oxoindolin-3-ylidene) butanoates and allenoates furnished 2,3,5-substituted tetrahydrofuran furan derivatives with oxindole moieties and two exocyclic double bonds in high yield. During this reaction, two carbon atoms and one oxygen atom of 3-oxo-4-(2-oxoindolin-3-ylidene) butanoates participated. Moreover, four isomers were synthesized and two of them can be isolated in this reaction.

ChemInform Abstract: 2,3‐Dihalo‐1‐propenes as Building Blocks in Cu(I)‐Catalyzed Domino Reactions: Efficient and Selective Synthesis of Furans.

AbstractTrisubstituted furans are synthesized in an efficient and selective one‐pot process by reacting dibromopropenes with 1,3‐dicarbonyl compounds.

ChemInform Abstract: Lewis Acid Catalyzed Unprecedented [3 + 2] Cycloaddition Yields 3,3′‐Pyrrolidinyldispirooxindoles Containing Four Contiguous Chiral Stereocenters with Two Contiguous Quaternary Spirostereocenters.

A Lewis acid catalyzed domino reaction cascades through azide–alkene cycloaddition, rearrangement, aziridine ring opening, and azomethine cycloaddition with a parent dipolarophile, resulting in 3,3′-pyrrolidinyldispirooxindoles containing four contiguous chiral stereocenters with two contiguous quaternary spirostereocenters.

Cu(II)-catalyzed domino reaction of 2-halobenzamide and arylmethanamine to construct 2-aryl quinazolinone

A novel method for achieving a copper(II)-catalyzed domino reaction for the construction of 2-aryl quinazolinones, without the addition of any ligand and additive, has been developed. The domino reaction achieved N-(alpha-substituted)benzylation, benzylic C-H amidation, and C-C (or C-H) bond cleavage. (C) 2014 Li-Xia Wang and Ya-Lin Tang. Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. All rights reserved.

Enzymatic multicomponent reaction for simultaneous synthesis of two important scaffolds, pyridin-2-ones and α-alkylated nitriles

An efficient approach for the synthesis of highly substituted pyridin-2-one derivatives and α-alkylated nitriles through enzymatic multicomponent reaction (MCR) was developed. This MCR involved bio-mimetic reduction between 3,4-dihydropyridin-2-one and activated olefin, both of which were in situ generated in the Acylase Amano (AA)-catalyzed domino reaction starting from benzaldehyde, cyanoacetamide and ketone. A wide range of substituted benzaldehydes and ketones were accepted by this reaction. Both final products (pyridin-2-one derivatives and α-alkylated nitriles) were important skeletons and synthetic intermediates. The synthetic application of prepared α-alkylated nitrile was demonstrated by converting it into the corresponding α-alkyl-β2-amino acid with high yield.

ChemInform Abstract: CuI‐Catalyzed C—N Bond Formation and Cleavage for the Synthesis of Benzimidazo[1,2‐a]quinazoline Derivatives.

A copper(I)-catalyzed domino reaction of N-(2-benzimidazolyl)-2-aminobenzamide and 2-halogenated benzaldehyde has been studied. The procedure is based on a sequential CuI-catalyzed Ullmann reaction (C–N bond formation) and two bond cleavage reactions and provides an efficient strategy for the synthesis of benzimidazo[1,2-a]quinazolines catalyzed by CuI/l-proline.

ChemInform Abstract: A Trifluoroacetic Acid Catalyzed Domino Reaction as an Approach to Amino Acid Derived 2,3‐Dihydro‐1H‐1,5‐benzodiazepines.

AbstractThe strategy allows the preparation of a library of benzodiazepines with potential pharmaceutical and biological activity.

2,3-Dihalo-1-propenes as building blocks in Cu(I)-catalyzed domino reactions: efficient and selective synthesis of furans.

The Cu(I)-catalyzed reaction of 2,3-dibromo-1-propenes with β-ketoesters and 1,3-diketones, respectively, in DMF at 120 °C using Cs2CO3 as a base and hydroquinone as an additive exclusively delivers 2,3,5-trisubstituted furans and related compounds with yields up to 96%. The highly regioselective domino process is based on an intermolecular C-allylation followed by an intramolecular Ullmann type O-vinylation and a double bond isomerization.

ChemInform Abstract: n‐Bu4NI‐Catalyzed Selective Dual Amination of sp3 C—H Bonds: Oxidative Domino Synthesis of Imidazo[1,5‐c]quinazolines on a Gram‐Scale.

An n-Bu4NI catalyzed domino reaction that involves selective dual amination of sp3 C–H bonds has been developed. The protocol affords a facile and efficient approach to the synthesis of imidazo[1,5-c]quinazolines under mild conditions.

Lewis acid catalyzed unprecedented [3 + 2] cycloaddition yields 3,3'-pyrrolidinyldispirooxindoles containing four contiguous chiral stereocenters with two contiguous quaternary spirostereocenters.

A Lewis acid catalyzed domino reaction cascades through azide-alkene cycloaddition, rearrangement, aziridine ring opening, and azomethine cycloaddition with a parent dipolarophile, resulting in 3,3'-pyrrolidinyldispirooxindoles containing four contiguous chiral stereocenters with two contiguous quaternary spirostereocenters.

CuI-catalyzed C-N bond formation and cleavage for the synthesis of benzimidazo[1,2-a]quinazoline derivatives.

A copper(I)-catalyzed domino reaction of N-(2-benzimidazolyl)-2-aminobenzamide and 2-halogenated benzaldehyde has been studied. The procedure is based on a sequential CuI-catalyzed Ullmann reaction (C-N bond formation) and two bond cleavage reactions and provides an efficient strategy for the synthesis of benzimidazo[1,2-a]quinazolines catalyzed by CuI/L-proline.

Borax catalyzed domino reactions: synthesis of highly functionalised pyridines, dienes, anilines and dihydropyrano[3,2-c]chromenes

Borax, an innocuous, inexpensive, and a naturally occurring material, very efficiently catalyzes the Knoevenagel condensation and Michael addition in domino fashion for the construction of highly functionalised pyridines, dienes, anilines and dihydropyrano[3,2-c]chromenes. The present protocol offers advantages in terms of higher yields, wide scope of substrates, operational simplicity, short reaction time, no requirement of workup or column chromatography, and easy access to a wide range of structurally diverse functionalized molecules of biological importance. Recycling of the catalyst and scaling up of the reactions are important attributes of this catalytic process.

ChemInform Abstract: Copper‐Catalyzed Domino Synthesis of Quinazolin‐4(3H)‐ones from (Hetero)arylmethyl Halides, Bromoacetate, and Cinnamyl Bromide.

Alkyl halides, including heteroarylmethyl and arylmethyl halides, bromoacetate, and cinnamyl bromide, are readily prepared via halogenation from basic raw materials, even using green processes. It is essential to replace their downstream products with them to prepare medicinally important heterocycles quinazolin-4(3H)-ones. Copper(I) bromide catalyzed domino reaction of alkyl halides and anthranilamides under air affords 2-substituted quinazolin-4(3H)-ones in good to excellent yields and with wide functional group tolerance. A mechanism for a copper(I) bromide involved organometal-catalyzed reaction via a four-step domino reaction is proposed.

Palladium(0)-Catalyzed Methylenecyclopropanation of Norbornenes with Vinyl Bromides

Highly strained methylenecyclopropane derivatives have been achieved via a novel and efficient Pd(0)-catalyzed domino reaction. The formal [2 + 1] cycloaddition reaction of vinyl bromides to norbornenes involves a Heck-type coupling and a C(sp(2))-H bond activation.

A Trifluoroacetic Acid Catalyzed Domino Reaction as an Approach to Amino Acid Derived 2,3-Dihydro-1H-1,5-benzodiazepines

Trifluoroacetic acid catalyzed condensation of aromatic amines with substituted benzaldehydes followed by intramolecular cyclization furnishes a highly effective synthesis of amino acid derived 2,3-dihydro-1H-1,5-benzodiazepines. The strategy provides an efficient access to a library of benzodiazepines that can be explored for potential pharmaceutical or biological activities.

New Palladium‐Catalyzed Domino Reaction with Intramolecular Ring Closure of an N‐(2‐Chloro‐3‐heteroaryl)arylamide: First Synthesis of Oxazolo[4,5‐b]pyrazines

AbstractThe synthesis of novel planar heterocycles is at the heart of basic research as such scaffolds constitute key building blocks in important diverse areas of research: drug discovery, material sciences, and pesticides. The well‐known benzoxazole is often contained in drug candidates but tweaking its lipophilicity and target interaction points are often desired. In this respect, the oxazolo[4,5‐b]pyrazine is an attractive heterocyclic scaffold as it possesses increased water solubility as well as two additional hydrogen bonding acceptors. We here report a new Pd(II)‐catalyzed domino reaction comprising the first Pd(II)‐assisted intramolecular cyclization of an N‐(2‐chloro‐3‐heteroaryl)arylamide and validate its value by application to the first synthesis of 2‐substituted oxazolo[4,5‐b]pyrazines. We demonstrate that a bidentate phosphorus ligand as well as the presence of an aromatic nitrogen atom is required for the domino reaction to proceed. The robustness of the methodology is confirmed by the synthesis of 23 2‐substituted oxazolo[4,5‐b]pyrazine analogues in good‐to‐high yields and containing both electron‐withdrawing as well as electron‐donating substituents on the reacting arylamide.magnified image

FeCl3·6H2O catalyzed aqueous media domino synthesis of 5-monoalkylbarbiturates: water as both reactant and solvent

Water as both reactant and solvent in a FeCl3·6H2O catalyzed domino reaction towards 5-monoalkylbarbiturates is described.

Reaction of 6-aminouracils with aldehydes in water as both solvent and reactant under FeCl3·6H2O catalysis: towards 5-alkyl/arylidenebarbituric acids

5-Alkyl/arylidenebarbituric acids were efficiently synthesized through an FeCl3·6H2O catalyzed domino reaction of 6-aminouracils, water and aldehydes with water serving a dual role as both solvent and reactant, under benign conditions.

Convenient synthesis of substituted tetrahydrofuran via Lewis base catalyzed [3 + 2] domino reactions

A DABCO catalyzed domino reaction between 3-oxo-4-(2-oxoindolin-3-ylidene) butanoates and allenoates furnished 2,3,5-substituted tetrahydrofuran furan derivatives bearing oxindole moiety and two exocyclic double bonds in high yield.

ChemInform Abstract: L‐Proline Catalyzed Domino Reactions for the Synthesis of Heterocycles

ChemInform Abstract: L‐Proline Catalyzed Domino Reactions for the Synthesis of Heterocycles