40652-40-2Relevant articles and documents
The Synthesis of Ketone-Derived Enamides by Elimination of HCN from Cyanoamides
Coussanes, Guilhem,Gaus, Katharina,O'Sullivan, Anthony C.
, p. 4176 - 4188 (2016/08/26)
Treatment of easily available ketone-derived cyanoamides with NaOtBu leads to enamides in a simple, scalable, and inexpensive one-step operation in good yield. Enamides not stabilized by conjugation or by inclusion in a ring can also be prepared. An E1cB mechanism consistent with all results and observations, is proposed. The Z geometry of the product enamide is highly favoured, and the regioselectivity can be directed by one′s choice of protecting group.
Multicomponent reactions of cyclobutanones
Pirrung, Michael C.,Wang, Jianmei
scheme or table, p. 2958 - 2963 (2009/09/05)
Cyclobutanones are essentially unknown as reactants in isonitrile-based multicomponent reactions. Ugi reactions of cyclobutanone and Passerini reactions of tetramethylcyclobutane-1,3-dione have been performed in this work. These reactions are significantly enhanced by being conducted in water, a subject of recent interest whose basis is still in question but whose effects are beyond doubt. The Ugi reaction of cyclobutanone has been used in a brief synthesis of an aspartame analogue.
Multicomponent synthesis of novel amino acid-nucleobase chimeras: aA versatile approach to PNA-monomers
Maison, Wolfgang,Schlemminger, Imre,Westerhoff, Ole,Martens, Juergen
, p. 1343 - 1360 (2007/10/03)
This paper describes a multicomponent approach to novel totally protected precursors of PNA-monomers via Ugi 4CC. The obtained bisamides are converted into several partially protected PNA-monomers or derivatives thereof using three different procedures. Methods for hydrolysis are shown to be dependent on the nature of the isocyano component required for Ugi 4CC. Several novel monomers suitable for oligomer synthesis are prepared demonstrating the high versatility of the reaction sequence. Copyright (C) 2000 Elsevier Science Ltd.
Postcondensation modifications of Ugi four-component condensation products: 1-Isocyanocyclohexene as a convertible isocyanide. Mechanism of conversion, synthesis of diverse structures, and demonstration of resin capture
Keating,Armstrong
, p. 2574 - 2583 (2007/10/03)
The concept of a 'universal isocyanide' that enables postcondensation modification of Ugi four-component condensation products is introduced. This strategy is suited for the synthesis of libraries. By using 1-isocyanocyclohexene as the isocyanide input in the Ugi reaction, the product cyclohexenamides can be converted to a variety of products. From the original α-(acylamino) amides, new carboxylic acids, esters, and thioesters are produced from acid-activated conversion of the cyclohexenamide moiety. It has been determined that the intermediate in conversion of this type is an oxazolinium-5-one (munchnone) that reacts with many nucleophiles to yield the products above. The munchnone can also undergo cycloaddition with acetylenic dipolarophiles to form pyrroles. Through internal nucleophilic attack, Ugi products are shown to convert to a protected monosaccharide derivative and to 1,4-benzodiazepine-2,5-diones. All of the conversions described consist of a single step. Resin capture of Ugi products is demonstrated, in which a solution condensation reaction is followed by trapping of the products onto solid support resin. Both the trapping step and subsequent cleavage of products from the resin occur in very high yield.
A New And Mild Procedure For The Preparation Of Vinyl Formamides From Thiooximes
Baldwin, J.E.,Aldous, D.J.,ONeil, I.A.
, p. 2051 - 2054 (2007/10/02)
Treatment of thiooximes with triphenylphosphine and acetic formic anhydride in dichloromethane at room temperature gives good yields of vinyl formamides under essentially neutral conditions.
REDUCTIVE FORMYLATION OF OXIMES; AN APPROACH TO THE SYNTHESIS OF VINIL ISONITRILES
Barton, H. R. Derek,Bowles, Timothy,Husinec, Suren,Forbes, Judith E.,Llobera, Antonia,et al.
, p. 3343 - 3346 (2007/10/02)
Reduction of ketoximes using anhydrous titanium-(III)-acetate in the presence of mixed formic-acetic anhydride yields N-formyl enamines whichmay be dehydrate to vinyl isonitriles
