Synthesis of N -Heterocycles - Organic Chemistry Portal

In this feature article, a general perspective of the research program aimed towards the preparation of polycyclic heterocycles by the means of enantioselective organocatalytic multicomponent reactions is presented. Guidelines for reaction design, including the selection of substrates and organocatalysts are discussed. For all transformations, scope and limitations are presented, along with post-functionalization to afford diversified heterocyclic scaffolds.1 Introduction2 Type I Products: 1,4,5,6-Tetrahydropyridines3 Type II Products: 1,2,3,4-Tetrahydropyridines4 Type III Products: Bridged Perhydropyridines5 Conclusion and Perspective

Multicomponent Reactions to Form Heterocycles by …

synthesis of heterocycles via multicomponent reactions …

Small Heterocycles in Multicomponent Reactions

Feng Shi received her B.S. and M.S. degrees from Xuzhou Normal University. In 2010, she joined the group of Prof. Gong to pursue her Ph.D. degree. Her research focuses on asymmetric multicomponent reactions leading to the synthesis of bioactive heterocycles.

Synthesis of Heterocycles via Multicomponent Reactions …

Scott E. Allen was born in 1984 in Kutztown, Pennsylvania. He received his B.S. in chemistry from Penn State University, where he performed undergraduate research with Dr. Xumu Zhang. He then joined the laboratory of Dr. Marisa C. Kozlowski at the University of Pennsylvania, where his research focused on computational organic chemistry studies of N-heterocyclic carbene-catalyzed reactions in collaboration with Dr. Jeffery Bode at the ETH. Upon completion of his Ph.D. in early 2013, Scott joined the laboratory of Dr. Albert Bowers at the UNC Eshelman School of Pharmacy as a postdoctoral associate.


Most Cited Heterocycles Articles - Elsevier

N2 - Multicomponent reactions (MCRs) are extremely popular owing to their facile execution, high atom-efficiency and the high diversity of products. MCRs can be used to access various heterocycles and highly functionalized scaffolds, and thus have been invaluable tools in total synthesis, drug discovery and bioconjugation. Traditional isocyanide-based MCRs utilize an external nucleophile attacking the reactive nitrilium ion, the key intermediate formed in the reaction of the imine and the isocyanide. However, when reactants with multiple nucleophilic groups (bisfunctional reactants) are used in the MCR, the nitrilium intermediate can be trapped by an intramolecular nucleophilic attack to form various heterocycles. The implications of nitrilium trapping along with widely applied conventional isocyanide-based MCRs in drug design are discussed in this review.

multicomponent syntheses of heterocycles

AB - Multicomponent reactions (MCRs) are extremely popular owing to their facile execution, high atom-efficiency and the high diversity of products. MCRs can be used to access various heterocycles and highly functionalized scaffolds, and thus have been invaluable tools in total synthesis, drug discovery and bioconjugation. Traditional isocyanide-based MCRs utilize an external nucleophile attacking the reactive nitrilium ion, the key intermediate formed in the reaction of the imine and the isocyanide. However, when reactants with multiple nucleophilic groups (bisfunctional reactants) are used in the MCR, the nitrilium intermediate can be trapped by an intramolecular nucleophilic attack to form various heterocycles. The implications of nitrilium trapping along with widely applied conventional isocyanide-based MCRs in drug design are discussed in this review.

Small Heterocycles in Multicomponent Reactions | …

Optically pure nitrogenous compounds, and especially nitrogen-containing heterocycles, have drawn intense research attention because of their frequent isolation as natural products. These compounds have wide-ranging biological and pharmaceutical activities, offering potential as new drug candidates. Among the various synthetic approaches to nitrogenous heterocycles, the use of asymmetric multicomponent reactions (MCRs) catalyzed by chiral phosphoric acids has recently emerged as a particularly robust tool. This method combines the prominent merits of MCRs with organocatalysis, thus affording enantio-enriched nitrogenous heterocyclic compounds with excellent enantioselectivity, atom economy, bond-forming efficiency, structural diversity, and complexity. In this Account, we discuss a variety of asymmetric MCRs catalyzed by chiral phosphoric acids that lead to the production of structurally diverse nitrogenous heterocycles.

Metal-Catalyzed Multicomponent Synthesis of Heterocycles

Description :Contents: L. Banfi ∙ A. Basso ∙ R. Riva: Synthesis of Heterocycles Through Classical Ugi and Passerini Reactions Followed by Secondary Transformations Involving One or Two Additional Functional Gr...

Science of Synthesis: Multicomponent Reactions.

This work describes the synthesis of compounds containing thiazolidine and propargylamidic motifs. Their preparation follows a synthetic route containing two multicomponent reactions. First, the Asinger four-component reaction is used to prepare 3-thiazolines and 3-oxazolines. Secondly, these heterocyclic imines are converted into propargylamides by a copper-catalyzed three-component reaction using acyl chlorides and terminal alkynes. The synthetic route is characterized by mild conditions and many functional groups are tolerated. The formation of an unexpected α-alkynoxyamide is also presented.