Literature DB >> 23559684

Ugi/Robinson-Gabriel reactions directed toward the synthesis of 2,4,5-trisubstituted oxazoles.

Arthur Y Shaw1, Zhigang Xu, Christopher Hulme.   

Abstract

This Letter discloses a novel concise synthesis of a series of 2,4,5-trisubstituted oxazoles via a tandem Ugi/Robinson-Gabriel sequence. Herein, 2,4-dimethoxybenzylamine 1 was used as an ammonia equivalent in combination with arylglyoxal 3 and supporting Ugi reagents, an isonitrile and carboxylic acid. As such the product of the acid treated Ugi intermediate is ideally configured to undergo a Robinson-Gabriel cyclodehydration reaction to yield the desired oxazole scaffold 5.

Entities:  

Keywords:  2,4,5-Trisubstituted oxazoles; Multicomponent reactions; Robinson–Gabriel reaction; Ugi reaction; Vilsmeier–Haack reaction

Year:  2012        PMID： 23559684      PMCID： PMC3613284          DOI： 10.1016/j.tetlet.2012.02.030

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  29 in total

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2.  Oxazole synthesis with minimal purification: synthesis and application of a ROMPgel Tosmic reagent.

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4.  A novel multicomponent synthesis of polysubstituted 5-aminooxazole and its new scaffold-generating reaction to pyrrolo[3,4-b]pyridine.

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5.  Facile preparation of oxazole-4-carboxylates and 4-ketones from aldehydes using 3-oxazoline-4-carboxylates as intermediates.

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6.  A practical method for oxazole synthesis by cycloisomerization of propargyl amides.

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7.  Three-component synthesis of highly functionalized 5-acetyloxazoles.

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9.  A four component coupling strategy for the synthesis of D-phenylglycinamide-derived non-covalent factor Xa inhibitors.

Authors:  Scott M Sheehan; John J Masters; Michael R Wiley; Stephen C Young; John W Liebeschuetz; Stuart D Jones; Christopher W Murray; Jeffrey B Franciskovich; David B Engel; Wayne W Weber; Jothirajah Marimuthu; Jeffrey A Kyle; Jeffrey K Smallwood; Mark W Farmen; Gerald F Smith
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10.  A new consecutive three-component oxazole synthesis by an amidation-coupling-cycloisomerization (ACCI) sequence.

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4.  Applications of ortho-phenylisonitrile and ortho-N-Boc aniline for the two-step preparation of novel bis-heterocyclic chemotypes.

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5.  Hydrazine-mediated cyclization of Ugi products to synthesize novel 3-hydroxypyrazoles.

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Review 6.  Two decades of recent advances of Ugi reactions: synthetic and pharmaceutical applications.

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Review 7.  Isocyanide-based multicomponent reactions towards cyclic constrained peptidomimetics.

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8.  Development of a method for the synthesis of 2,4,5-trisubstituted oxazoles composed of carboxylic acid, amino acid, and boronic acid.

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9.  Doebner-type pyrazolopyridine carboxylic acids in an Ugi four-component reaction.

Authors:  Maryna V Murlykina; Oleksandr V Kolomiets; Maryna M Kornet; Yana I Sakhno; Sergey M Desenko; Victoriya V Dyakonenko; Svetlana V Shishkina; Oleksandr A Brazhko; Vladimir I Musatov; Alexander V Tsygankov; Erik V Van der Eycken; Valentyn A Chebanov
Journal:  Beilstein J Org Chem       Date:  2019-06-12       Impact factor: 2.883
  9 in total

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