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UGI REACTION, MULTICOMPONENT SYNTHESIS - …
Commun., 353-359 (2004) "A Versatile Synthesis of -Amino Acid Derivatives Via the Ugi Four-Component Condensation with a Novel Convertible Isonitrile," Kentaro Rikimaru, Arata Yanagisawa, Toshiyuki Kan, Tohru Fukuyama Synlett, 41-44 (2004) 2003 "Synthesisof Secondary Arylamines through Copper-Mediated Intermolecular ArylAmination,"Kentaro Okano, Hidetoshi Tokuyama, Tohru FukuyamaOrg.
A three step synthesis of N-unsubstituted tetrazolo γ- and δ-lactams involving a key Ugi-4CR is presented. The compounds, otherwise difficult to access, are conveniently synthesized in overall good yields by our route. PDB analysis of the N-unsubstituted γ- and δ-lactam fragment reveals a strongly tri-directional hydrogen bond donor acceptor interaction with the amino acids of the binding sites.
An improved methodology for synthesis of new Ugi …
We have designed a fast and reliable synthetic route to 5- and 6-membered unsubstituted tetrazololactams using a key azido-Ugi reaction, followed by a deprotection and cyclisation step. Analysis of the scaffold in the protein data bank indicates that the lactam-NH can undergo multiple and strong H-bonds. Moreover the scaffold is underused in medicinal chemistry and thus provides multiple chances for drug design.
The Ugi tetrazole synthesis was initially performed under Ugi azide conditions with tritylamine (1), azidotrimethylsilane (2), phenylethylisonitrile and various aldehyde esters to check scope and limitations. The aliphatic aldehydes 3a-b were prepared according to previous described methods starting from the acid chloride (.).
Thiazole synthesis - Organic chemistry
Synthesis of Functionalized Quinolines via Ugi and Pd-CatalyzedIntramolecular Arylation Reactions Zhibo Ma, Zheng Xiang,Tuoping Luo, Kui Lu, Zhibin Xu, Jiahua Chen, and Zhen Yang J.
Ammonia is one of the few amine components which does not regularly give convincing results in the Ugi MCRs.- Therefore we recently introduced tritylamine as an ammonia surrogate in the Ugi tetrazole MCR. This reaction forms the core of our design of a synthetic pathway towards N-unsubstituted γ- and δ-lactams (). The first step comprises the Ugi tetrazole MCR using tritylamine, followed by cleavage of the trityl group. The formed primary amine should easily undergo cyclisation to form the target γ- and δ-lactam compounds.
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Named Reactions List - The Organic Synthesis Database
T1 - Applications of N-BOC-diamines for the solution phase synthesis of ketopiperazine libraries utilizing a Ugi/De-BOC/Cyclization (UDC) strategy
The first total synthesis of racemic perophoramidine is described
Using theprinciples of , theUgi reaction offers the possibility to synthesize a great number ofdifferent compounds in one reaction, by the reaction of variousketones (or aldehydes), amines, isocyanides and carboxylic acids.
IPCC - Intergovernmental Panel on Climate Change
Using the Ugi reactionin combination with other reactions enlarges the chemical diversityof possible products.Examples of Ugi reaction combinations: can be prepared using the Ugireaction.Additionally, many of the caine-type anesthetics aresynthesized using this reaction.
The Intergovernmental Panel on Climate Change was created in 1988
Stereocontrolled formal total synthesis of proteasome inhibitor omuralide is described. This is featured by the application of Ugi 4–center 3–component condensation reaction to prepare a highly functionalized pyroglutamic acid. To this end, a novel convertible isocyanide was developed, which is readily available by preparative synthesis from nitrotoluene. The hydrolysis of the sterically hindered –terminal amide derived from the isocyanide was facilitated by the conversion to –acylindole. By careful design of the γ–ketoacid precursor, a substrate–controlled diastereoselective Ugi reaction was successfully accomplished. Also, several highly functionalized pyroglutamic acid amides were prepared with high diastereoselectivity.
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