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Isocyanide based multicomponent reactions of oxazolidines and related systems

Waller, RW; Diorazio, LJ; Taylor, BA; Motherwell, WB; Sheppard, TD; (2010) Isocyanide based multicomponent reactions of oxazolidines and related systems. TETRAHEDRON , 66 (33) 6496 - 6507. 10.1016/j.tet.2010.05.083.

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Abstract

N-Alkyloxazolidines react in a multicomponent reaction with carboxylic acids and isocyanides to give N-acyloxyethylamino acid amides. The previously reported reaction conditions were improved using a design of experiments approach (DoE). Under the optimised conditions, good yields of the N-acyloxyethylamino acid amide products are obtained both via a three- or four-component approach from N-alkylethanolamines, aldehydes/ketones, isocyanides and carboxylic acids. The reaction of oxazolidines without a nitrogen substituent was found to give either the expected Ugi products or the N-acyloxyethylamino acid amides depending on the choice of reaction conditions. Optimised reaction conditions were also developed for the ring-expansion of oxazolidines to morpholin-2-ones via reaction with an isocyanide followed by hydrolysis. The mechanistic pathway of the multicomponent reaction was briefly investigated using an O-18 labelling experiment. The carboxylic acid component can be replaced by a range of other acidic nucleophiles including thiobenzoic acid, thiophenol or 5-phenyltetrazole, which are incorporated via an alternative pathway. These latter reactions can also be applied to 2-aminotetrahydrofurans, 2-aminotetrahydropyrans or 4-hydroxybut-2-one, further extending the structural diversity of the multicomponent reaction products. (C) 2010 Elsevier Ltd. All rights reserved.

Type:Article
Title:Isocyanide based multicomponent reactions of oxazolidines and related systems
Location:Paris, FRANCE
DOI:10.1016/j.tet.2010.05.083
Keywords:Multicomponent reactions, Isocyanides, Design of experiments, Oxazolidines, Ring-opening reactions, UGI-SMILES COUPLINGS, C-O BOND, GLYCOLALDEHYDE DIMER, 4-COMPONENT REACTION, REDUCTIVE CLEAVAGE, CARBOXYLIC-ACIDS, PRIMARY AMINES, ACETALS, THIOLS, STRATEGIES
UCL classification:UCL > School of BEAMS > Faculty of Maths and Physical Sciences > Chemistry

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