Multicomponent Domino Reaction Research Articles

Selective synthesis of polyfunctionalized pyrido[2,3-b]indoles by multicomponent domino reactions.

A series of novel polyfunctionalized pyrido[2,3-b]indoles were synthesized by three- or four-component domino reactions under microwave irradiation. This protocol has the advantages of readily available starting materials, short reaction times, high yields, easy workup, and high chemo- and regioselectivities.

Synthesis of new class of spirocarbocycle derivatives by multicomponent domino reaction and their evaluation for antimicrobial, anticancer activity and molecular docking studies

A series of 25 new spirocarbocycles were synthesized by a three component reaction that involves few cyclic nucleophiles, vinyl malononitriles and aldehydes with variable substitution patterns. All the synthesized compounds were evaluated for their antimicrobial activity and the compounds showed significant activity. Synthesized compounds 4c, 4i and 6i showed good anticancer activity against A549 cancer cell line. Molecular docking studies indicated that compound 4i had the greatest affinity for DNA gyrase receptor than others and compound 6i had the greatest affinity for anaplastic lymphoma kinase (ALK) receptor. These compounds can be better therapeutic agents for microbial and cancer cell lines.

A Novel Route for the Diastereoselective Synthesis of Dispiro[tetrahydroquinoline‐bis(2,2‐dimethyl[1,3]dioxane‐4,6‐dione)] Derivatives via a One‐Pot Domino Multicomponent Reaction of Arylamines, Aromatic Aldehydes, and Meldrum's Acid

A protocol has been developed for the diastereoselective synthesis of dispiro[tetrahydroquinoline‐bis(2,2‐dimethyl[1,3] dioxane‐4,6‐dione)] derivatives via a one‐pot domino multicomponent reaction of arylamines, aromatic aldehydes, and Meldrum's acid for the first time. The products, with remarkable diastereoselectivity, were successfully synthesized in acetic acid media in ambient temperature along with the suggested mechanism through combination of domino Knoevenagel, Michael, and Diels–Alder reactions. The products have been characterized by IR, mass, 1H NMR, 13C NMR spectroscopy, and elemental analyses. The stereoselectivity of compounds was established with crystallography and NMR spectroscopy.

ChemInform Abstract: Regioselective Multicomponent Domino Reactions Providing Rapid and Efficient Routes to Fused Acridines.

ChemInformVolume 45, Issue 23 Heterocyclic Compounds ChemInform Abstract: Regioselective Multicomponent Domino Reactions Providing Rapid and Efficient Routes to Fused Acridines. Bo Jiang, Bo Jiang Sch. Chem. Chem. Eng., Jiangsu Norm. Univ., Jiangsu, Xuzhou 221116, Peop. Rep. ChinaSearch for more papers by this authorShu-Jiang Tu, Shu-Jiang Tu Sch. Chem. Chem. Eng., Jiangsu Norm. Univ., Jiangsu, Xuzhou 221116, Peop. Rep. ChinaSearch for more papers by this authorGuigen Li, Guigen Li Sch. Chem. Chem. Eng., Jiangsu Norm. Univ., Jiangsu, Xuzhou 221116, Peop. Rep. ChinaSearch for more papers by this authorJin-Peng Zhang, Jin-Peng Zhang Sch. Chem. Chem. Eng., Jiangsu Norm. Univ., Jiangsu, Xuzhou 221116, Peop. Rep. ChinaSearch for more papers by this authorWei Fan, Wei Fan Sch. Chem. Chem. Eng., Jiangsu Norm. Univ., Jiangsu, Xuzhou 221116, Peop. Rep. ChinaSearch for more papers by this authorJie Ding, Jie Ding Sch. Chem. Chem. Eng., Jiangsu Norm. Univ., Jiangsu, Xuzhou 221116, Peop. Rep. ChinaSearch for more papers by this author Bo Jiang, Bo Jiang Sch. Chem. Chem. Eng., Jiangsu Norm. Univ., Jiangsu, Xuzhou 221116, Peop. Rep. ChinaSearch for more papers by this authorShu-Jiang Tu, Shu-Jiang Tu Sch. Chem. Chem. Eng., Jiangsu Norm. Univ., Jiangsu, Xuzhou 221116, Peop. Rep. ChinaSearch for more papers by this authorGuigen Li, Guigen Li Sch. Chem. Chem. Eng., Jiangsu Norm. Univ., Jiangsu, Xuzhou 221116, Peop. Rep. ChinaSearch for more papers by this authorJin-Peng Zhang, Jin-Peng Zhang Sch. Chem. Chem. Eng., Jiangsu Norm. Univ., Jiangsu, Xuzhou 221116, Peop. Rep. ChinaSearch for more papers by this authorWei Fan, Wei Fan Sch. Chem. Chem. Eng., Jiangsu Norm. Univ., Jiangsu, Xuzhou 221116, Peop. Rep. ChinaSearch for more papers by this authorJie Ding, Jie Ding Sch. Chem. Chem. Eng., Jiangsu Norm. Univ., Jiangsu, Xuzhou 221116, Peop. Rep. ChinaSearch for more papers by this author First published: 22 May 2014 https://doi.org/10.1002/chin.201423166Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume45, Issue23June 10, 2014 RelatedInformation

Domino Reaction of Arylglyoxals with Pyrazol-5-amines: Selective Access to Pyrazolo-Fused 1,7-Naphthyridines, 1,3-Diazocanes, and Pyrroles

New multicomponent domino reactions of arylglyoxals with pyrazol-5-amines have been established, providing selective access to unprecedented pyrazolo-fused 1,7-naphthyridines, 1,3-diazocanes, and pyrroles (up to 52 examples). The unreported dipyrazolo-fused 1,7-naphthyridines were regioselectively synthesized through a special double [3 + 2 + 1] heteroannulation accompanied by direct C–C formation between two electrophilic sites of arylglyoxals. The unusual [3 + 3 + 1 + 1] cyclization resulted in 20 examples of novel dipyrazolo-fused 1,3-diazocanes, whereas pyrrolo[2,3-c]pyrazoles were obtained in good yields by varying arylglyoxals 1 and pyrazol-5-amines 2 in the ratio 1:2. Mechanisms of formation of these three new types of heterocycles are also proposed.

ChemInform Abstract: A β‐Enaminone‐Initiated Multicomponent Domino Reaction for the Synthesis of Indoloquinolizines and Benzoquinolizines from Acyclic Precursors.

The cerium(IV) ammonium nitrate (CAN)-catalyzed sequential multicomponent reaction between tryptamine, α,β-unsaturated aldehydes, and β-dicarbonyl compounds affords highly substituted indolo[2,3-a]quinolizines in a single synthetic operation. Two rings are generated through the creation of two CC and two CN bonds by a domino process comprising initial β-enaminone formation, followed by individual Michael addition, 6-exo-trig cyclization, iminium formation, and Pictet–Spengler steps. Furthermore, the reaction is diastereoselective and affords exclusively compounds with a trans relationship between the H-2 and H-12b protons. The use of amines bearing a less nucleophilic side chain aromatic ring (5-bromotryptamine, 3,4-dimethoxyphenylethylamine) prevents the Pictet–Spengler final step and leads to N-indolylethyl or N-phenylethyl-1,4-dihydropyridines, which are cyclized to the corresponding indolo[2,3-a]quinolizines or benzo[a]quinolizines in the presence of HCl in methanol/water. Treatment of the fused quinolizine derivatives with sodium triacetoxyborohydride led to the corresponding indolo[2,3-a]quinolizidines or benzo[a]quinolizidines, possessing four stereogenic centers, as mixtures of two diastereomers.

A rapid and high efficient microwave promoted multicomponent domino reaction for the synthesis of spirooxindole derivatives

A simple, efficient and rapid method has been developed for synthesis of 6,6-dimethyl-4-phenyl-6,7-dihydro-1H-spiro[furo[3,4-b]quinoline-9,3′-indoline]1,2′,8(3H,4H,5H)-trione derivatives. These heterocycles were prepared through domino one-pot and multicomponent condensation reactions of isatins, dimedone, and anilinolactones in the presence of alum (15mol%) as an inexpensive, nontoxic, convenient, and available Lewis acid catalyst under microwave irradiation. The corresponding products have been obtained in excellent isolated yields between 78% and 90%, with high purity, in short reaction times about 10–12min and easy work up.

“On-water” synthesis of novel trisubstituted 1,3-thiazolesviamicrowave-assisted catalyst-free domino reactions

A clean, efficient and catalyst-free multicomponent domino reaction of arylglyoxals, cyclic 1,3-dicarbonyls and thioamides in aqueous media under microwave conditions is reported.

Efficient [4+1]/[3+2+1] bis-cyclizations stereoselectively yielding unprecedented polyacyclic indeno-fused xanthenes

Concise and efficient [4+1]/[3+2+1] bis-cyclizations of o-phthalaldehyde with cyclic 1,3-dicarbonyls have been established for the stereoselective synthesis of unprecedented polycyclic indeno[2,1-l]xanthene derivatives. The multicomponent domino reaction (MDR, AB2 type) is easy to perform by mixing inexpensive substrates in HOAc at room temperature. The present synthesis shows attractive properties such as the simple one-pot fashion, high bond-forming efficiency, and easy purifications. Up to two new rings and four sigma-bonds were achieved in these MDRs without using any metal catalysts.

A β‐Enaminone‐Initiated Multicomponent Domino Reaction for the Synthesis of Indoloquinolizines and Benzoquinolizines from Acyclic Precursors

The cerium(IV) ammonium nitrate (CAN)-catalyzed sequential multicomponent reaction between tryptamine, α,β-unsaturated aldehydes, and β-dicarbonyl compounds affords highly substituted indolo[2,3-a]quinolizines in a single synthetic operation. Two rings are generated through the creation of two C-C and two C-N bonds by a domino process comprising initial β-enaminone formation, followed by individual Michael addition, 6-exo-trig cyclization, iminium formation, and Pictet-Spengler steps. Furthermore, the reaction is diastereoselective and affords exclusively compounds with a trans relationship between the H-2 and H-12b protons. The use of amines bearing a less nucleophilic side chain aromatic ring (5-bromotryptamine, 3,4-dimethoxyphenylethylamine) prevents the Pictet-Spengler final step and leads to N-indolylethyl or N-phenylethyl-1,4-dihydropyridines, which are cyclized to the corresponding indolo[2,3-a]quinolizines or benzo[a]quinolizines in the presence of HCl in methanol/water. Treatment of the fused quinolizine derivatives with sodium triacetoxyborohydride led to the corresponding indolo[2,3-a]quinolizidines or benzo[a]quinolizidines, possessing four stereogenic centers, as mixtures of two diastereomers.

Highly Efficient Chemoselective Synthesis of Polysubstituted Pyrroles via Isocyanide-Based Multicomponent Domino Reaction

A multicomponent domino reaction for the chemoselective, catalyst-free synthesis of polysubstituted pyrroles from readily available isocyanides, primary or secondary amines, and gem-diactivated olefins has been developed. Structurally diverse pyrroles were obtained in moderate to good yields under mild conditions.

Rh<sub>2</sub>(OAc)<sub>4</sub>-AuCl<sub>3</sub>协同催化三组分串联反应高效构建异色烯衍生物

Multicomponent domino reactions can most unlimitedly improve reaction efficiency to construct complex molecules from simple materials. The intriguing Rh 2 (OAc) 4 and AuCl 3 synergistic catalysis in domino cyclization/three-component reactions of 2-alkyny-larylaldhydes with diazo compounds and alcohols are reported to successfully afford isochromenes skeleton in good yield and moderate to good diastereoselectivity, which can not realized with monocatalyst.

An efficient synthesis of novel spiro[benzo[c]pyrano[3,2-a]phenazines] via domino multi-component reactions using l-proline as a bifunctional organocatalyst

A novel, domino, multi-component reaction for the synthesis of polyfunctionalized spiro[benzo[c]pyrano[3,2-a]phenazine] derivatives has been established. l-Proline has been used as a bifunctional catalyst for the one-pot condensation of 2-hydroxy-1,4-naphthoquinone with aromatic 1,2-diamines to form the corresponding quinoxalines and then cyclo-condensation with an alkylmalonate and a cyclic carbonyl compound leads to novel spiro[benzo[c]pyrano[3,2-a]phenazine] derivatives in high yields and short reaction times.

Domino [3+2+1] heterocyclization of isothiocyanates with aryl amidines leading to polysubstituted 1,3,5-triazine derivatives

Concise and efficient domino [3+2+1] heterocyclization of isothiocyanates with aryl amidines has been established for the synthesis of 1,3,5-triazine derivatives. The multicomponent domino reaction (MDR, AB2 type) is easy to perform simply by mixing inexpensive isothiocyanates and aryl amidines in the presence of NaOH under microwave heating. The present synthesis shows attractive properties such as concise one-pot conditions, short reaction periods (15–24min), and easy purifications. The resulting 1,3,5-triazine derivatives are important structural motifs in organic and medicinal research.

Chemodivergent, multicomponent domino reactions in aqueous media: l-proline-catalyzed assembly of densely functionalized 4H-pyrano[2,3-c]pyrazoles and bispyrazolyl propanoates from simple, acyclic starting materials

A library of 4H-pyrano[2,3-c]pyrazol-6-amines was synthesized in excellent yield employing an L-proline-catalyzed, on-water four-component domino reaction from hydrazines, β-dicarbonyl compounds, nitriles and dialkyl acetylenedicarboxylates that generates two rings by the creation of C–C (two), C–N, CN and C–O bonds and presumably involves a sequence of hydrazone formation, cyclocondensation, Michael, [1,3]-hydrogen shift, Michael addition and 6-exo-dig annulation steps. When alkyl propiolates were employed, a three-component reaction took place furnishing alkyl 3,3-bis(5-hydroxy-1H-pyrazol-4-yl)propanoates via a double Michael domino process.

Multicomponent domino reactions: borax catalyzed synthesis of highly functionalised pyran-annulated heterocycles

A collection of pyrano[3,2-c] chromene, 4H-chromene and 4H-pyran were synthesized in excellent yield employing an innocuous, inexpensive and naturally occurring borax-catalyzed multicomponent domino reaction. The present protocol offers advantages in terms of higher yields, short reactions time and no workup and no column chromatography.

An eco-efficient, domino synthesis of highly functionalized spiro-oxindole derivatives catalyzed by an organocatalyst in an aqueous medium

Here we report a multicomponent domino reaction for the synthesis of a combinatorial library of spiro-oxindole derivatives with a pyrido[2,3-d]pyrimidine moiety by a one pot, eco-efficient three component reaction involving isatin, 6-aminouracil and acetyl acetone which is catalyzed by an organocatalyst in water as the reaction medium. A heterocyclic molecule which contains a highly functionalized bioactive spiro-oxindole and a pyrido[2,3-d]pyrimidine ring in one nucleus is very important due to its bioactive nature. This method avoids the use of costly and toxic catalysts and organic solvents which show a number of side effects on the environment and human beings. The simplicity and versatility of this eco-efficient method is described.

Molecular iodine catalyzed one-pot multicomponent reactions for the synthesis of dihydrochromeno[4,3-b]pyrazolo[4,3-e]pyridin-6(7H)-ones

A simple and concise method catalyzed by molecular iodine has been reported for the synthesis of a series of dihydrochromeno[4,3-b]pyrazolo[4,3-e]pyridin-6(7H)-ones (1) using a multicomponent domino reaction of aromatic aldehydes, 4-hydroxycoumarin derivatives and 3-aminopyrazoles. The same catalyst was also found useful for the four component reaction of aromatic aldehydes, 4-hydroxycoumarin, benzoylacetonitrile and hydrazine hydrate. The notable advantages of this method are: good yields, no column chromatography, environmentally friendly catalyst and applicability for diversity oriented synthesis of substituted dihydrochromeno pyrazolo pyridin-6(7H)-one scaffolds using both three and four component reactions.

Ultrasound promoted catalyst-free and selective synthesis of spiro[indole-3,4′-pyrazolo[3,4-e][1,4]thiazepines] in aqueous media and evaluation of their anti-hyperglycemic activity

A novel and catalyst-free aqueous mediated multicomponent domino reaction (MCR) capable of affording medicinally important spiro[indole-3,4′-pyrazolo[3,4-e][1,4]thiazepines] under sonication in excellent yield and in shorter time is reported. This new protocol provides a new seven-membered ring system selectively instead of the expected five-membered ring system or other possible isomers. The structure and relative stereochemistry of spiro products was established by single crystal X-ray analysis of a representative compound and spectroscopic techniques. In comparison to conventional synthesis, the advantages of this method are that it is catalyst-free, has an easy workup and uses water as the solvent which is considered to be relatively environmentally benign, and this work offers a new way to create molecular complexity with maximum simplicity. The representative compounds were screened for their ability to inhibit the enzyme α-amylase.

ChemInform Abstract: Multicomponent Domino Reactions of Acetylenedicarboxylates: Divergent Synthesis of Multi‐functionalized Pyrazolones and C‐Tethered Bispyrazol‐5‐ols.

AbstractThe reaction of equimolar amounts of aldehydes bearing electron‐donating aryl groups, hydrazines and esters (II) results in formation of pyrazolones.