Three-component Tandem Reaction Research Articles

Novel three-component tandem reactions of cyclic mono ketones, isatin and sarcosine: formation of dispiropyrrolidines

One-pot, three-component tandem reactions of cyclic mono ketones, isatin and sarcosine affording dispiropyrrolidines stereoselectively are reported for the first time.

A novel three-component tandem protocol for the regioselective synthesis of 1-(2-arylmethyl-5-aryl-3-thienyl)pyrrolidines and piperidines

A series of new substituted 1-(2-arylmethyl-5-aryl-3-thienyl)pyrrolidines and piperidines were synthesised by one-pot, three-component tandem reactions of 5-aryldihydro-3(2 H)-thiophenone, aromatic aldehydes and pyrrolidine/piperidine under solvent-free microwave irradiation. This facile transformation occurs presumably via a tandem enamine formation–carbonyl addition–dehydration–isomerisation sequence.

A Three-Component Tandem Reductive Aldol Reaction Catalyzed by N-Heterocyclic Carbene−Copper Complexes

[Structure: see text] An efficient catalytic system for the three-component coupling of electrophilic alkenes, aldehydes, and silane was optimized with a new family of copper N-heterocyclic carbene complexes. These catalysts do not require activation and show high activity (TOF>15,000 h-1) as well as some anti diastereoselectivity.

Mycophenolic Acid Is a Potent Inhibitor of Angiogenesis

Angiogenesis is necessary for the vascularization of a tumor, providing essential nourishment for tumor growth, and the progression and metastasis of cancer cells.1 Although tremendous efforts and resources have been dedicated to discovering angiogenesis inhibitors, very few candidates have been approved by FDA for therapeutic applications. Currently, Avastin (bevacizumab), a humanized monoclonal antibody, and Macugen (Pegaptanib), a pegylated oligonucleotide aptamer, both directed against vascular endothelial growth factor (VEGF) pathway, are two of the approved drugs for clinical use. There is still a great need to develop small molecule drugs for antiangiogenesis purpose. One approach to broaden the discovery platform is to identify antiangiogenic activities from existing drugs that have well defined toxicity and pharmacokinetics. Once a known drug is demonstrated to inhibit angiogenesis, it would move into the clinic trails more rapidly. Because most known drugs have well defined structures and defined biological targets, it is also possible to further improve the compound structure or select the target as a new entry point for angiogenesis-based studies and therapies. Currently there are more than 2000 known drugs that can be used for re-purposing applications. It would be desirable to have a single in vivo assay allowing rapid screening of a large number of compounds for new activities such as angiogenesis inhibition. Recently, the zebrafish has been shown to be a useful model organism for this type of approach.2,3 Zebrafish blood vessels form by angiogenic sprouting and appear to use the same pathways necessary for blood vessel growth in mammals.4 Using transgenic embryos expressing GFP in vessels, the embryonic blood vessels in live zebrafish can be directly …

One-Pot Synthesis of Macrocycles by a Tandem Three-Component Reaction and Intramolecular [3+2] Cycloaddition

By combining three appropriately designed simple substrates, a programmed sequence involving an alpha-isocyano acetamide-based three-component reaction followed by a copper-catalyzed intramolecular [3+2] cycloaddition of alkyne and azide took place to afford complex macrocycles in moderate to good yields. One macrocycle and two heterocycles were produced with concurrent formation of five chemical bonds in this operationally simple process.

Three-Component Tandem Reaction to Synthesize Tetrasubstituted Olefins

A stereoselective one-pot three-component allylzincation of acetylenic sulfones/Negishi cross-coupling of vinyl zinc bromides with halohydrocarbons is described. Tetrasubstituted olefins containing a 1,4-diene structural unit were prepared with complete regio- and stereocontrol. The allylzincation proceeded with syn-addition and the geometry of the double bond is preserved during the Negishi coupling.

Highly Regio- and Stereoselective Synthesis of Tetrasubstituted Olefins by the Three-Component Tandem Reaction of Allylzinc Bromide, Acetylenic Sulfone, and Halohydrocarbon

[reation: see text]. Tetrasubstituted olefins containing a 1,4-diene structural unit can be regio- and stereoselectively constructed in one pot by the allylzincation of acetylenic sulfones, followed by Negishi cross-coupling with halohydrocarbons in the presence of catalytic Ni(PPh3)2Cl2.

ESI-MS Studies on the Mechanism of Pd(0)-Catalyzed Three-Component Tandem Double Addition-Cyclization Reaction

Four cationic palladium intermediates have been characterized by the high-resolution ESI-FTMS technology, on the basis of which a mechanism was proposed for the Pd0-catalyzed three-component tandem double addition cyclization of organic halides, 2-(2,3-allenyl)malonates, and imines.

Synthesis of α-amino γ-lactone via a novel tandem three-component reaction of alkenes, glyoxylates and amines

α-Amino γ-lactones were generated by an InCl3-mediated or Sc(OTf)3-catalyzed three-component reaction of alkenes, glyoxylates and amines.