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Showing 1 to 12 of 12 for “"Trichloroacetimidates"”.
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Applying Trichloroacetimidates to the Synthesis of Benzylic Trichloroacetamides & Functionalized Indoles
<p>Allylic trichloroacetimidates have been previously shown to be versatile substrates for the synthesis of C-N bonds through [3,3]-sigmatropic rearrangements. This work explores a similar reaction, the rearrangement of benzylic trichloroacetimidates to access benzylic trichloroacetamides. The …
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CONVENIENT ETHERIFICATION USING TRICHLOROACETIMIDATES AND SYNTHESIS OF AMINOSTEROID SHIP INHIBITORS
… a reevaluation of the reactivity of alcohols and trichloroacetimidates has been undertaken. In many cases, simply heating the imidate with an alcohol in refluxing toluene without an exogenous acid or base is an effective method for the formation of the desired ether. This operationally simple …
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Thioetherification and Etherification Utilizing Trichloroacetimidates Under Thermal Conditions & Progress Towards an Efficient Synthesis of AQX-1125
… solely under thermal conditions utilizing trichloroacetimidates.</p> <p>The alkylation of thiols by the direct displacement of trichloroacetimidates has been accomplished under thermal conditions (heating in refluxing THF). These reactions proceed to the corresponding thioetherification …
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Trichloroacetimidates as Alkylating Reagents in C-N Bond Formation and Synthesis of Aminosteroid and Quinoline Inhibitors of Src Homology 2 Domain-Containing Inositol Phosphatase (SHIP)
<p>Trichloroacetimidates have frequently been used in the formation of glycosidic bonds and other ethers, which is especially useful for the introduction of ether protecting groups. Trichloroacetimidates have also been used as electrophiles in Friedel-Crafts alkylation reactions. The formation of …
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Exploration of Carbon-oxygen and Carbon-nitrogen Bond Formation Utilizing Trichloroacetimidates and Investigations of New Reactions Mediated By Oxoammonium Salts
… bulky groups onto one of the phenolic oxygens. Trichloroacetimidates are also shown to be useful reactions for the synthesis of esters. These reagents proceeded through a symbiotic activation pathway. Under these conditions sensitive substrates did not decompose, which often is observed with …
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Trichloroacetimidates As Outstanding Electrophiles for the Carbon-nitrogen, Carbon-oxygen and Carbon-carbon Bonds Formation and Synthetic Studies of Protein Phosphatase-5 (pp5) Small Molecule Inhibitors
<p>Trichloroacetimidates have been previously used for glycosidic bond formation in carbohydrate chemistry and in Friedel-Craft reactions. Traditionally, trichloroacetimidates had be synthesized using an alcohol and strongly basic conditions, but in recent years milder preparation methods have been …
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Trichloroacetimidates as Alkylating Reagents and Their Application in the Synthesis of Pyrroloindoline Natural Products and Synthesis of Small Molecule Inhibitors of Src Homology 2 Domain- Containing Inositol Phosphatase (SHIP)
<p>Trichloroacetimidates are known to be excellent alkylating agents when activated by a catalytic amount of a Brønsted or Lewis acid. Work described herein involved taking advantage of the favorable reactivity of trichloroacetimidates to establish several different synthetic protocols, including …
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Formation of Pyrroloindolines and Alkylation of N-heterocycles With Trichloroacetimidates and Synthesis of Quinoline Based Small Molecule Inhibitors of Ghrelin O-acyltransferase (goat)
… properties. Recently we have focused on using trichloroacetimidates for the synthesis of these fascinating molecules. Trichloroacetimidates can be used an electrophilic source of an alkyl group to form the pyrroloindoline directly from tryptamine derivatives. In this manner …
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A Modular Approach to Highly Functionalized Indole Derivatives and Syntheses of Tryptamine-based SHIP Inhibitors
… account of reactions of glycosyl or alkyl trichloroacetimidates with various indole derivatives substituted at N-, 2- and 3- position. While Friedel Crafts reactions of indoles with trichloroacetimidates are known, regioselectivity of these reactions is not very clear. The relative utility …
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Reactions for rapid access to C3a oxygenated pyrroloindolines and its application towards a novel route to pestalazine A
… in this work simply heating diarylmethyl trichloroacetimidates with the allyltributylstannane gives easy access to these systems. Electron rich benzylic trichloroacetimidate systems gave the best results, where excellent yields are achieved just by refluxing the reactants together in …
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Investigation of metal mediated reactions for natural product synthesis
… led to the synthesis of other substituted trichloroacetimidates. Rearrangement of these compounds demonstrated the role of steric strain on the stereocontrol of the rearrangement and also highlighted the role that solvent can have upon the diastereoselectivity of ether-directed …
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Synthesis of Hetero-chitooligosaccharides
Chitooligosaccharides are composed of linear β-(1→4)-linked 2-acetamido-2-deoxy-β-D-glucopyranose (GlcNAc) and/or 2-amino-2-deoxy-β-D-glucopyranose (GlcN). They are of interest due to their remarkable biological properties including antibacterial, antitumor, antifungal and elicitor activities. They …