Lewissäure‐katalysierte Umsetzung von Carbonylverbindungen mit tert.‐Butylisonitril

Müller, Eugen; Zeeh, Bernd

doi:10.1002/jlac.19666960108

Cited by 41 publications

(9 citation statements)

References 5 publications

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“…[77] Bicyclic, sterically extremely hindered ketones such as camphor or bicyclo[3.2.1]octanone-2 do not react with isocyanides in a Passerini reaction, even in the presence of BF 3´O Et 2 . [78] Besides normal C-isocyanides, Me 3 SiCN (TMSCN), which is in equilibrium with TMSNC and is a formal derivative of the most basic isocyanide, namely isocyanic acid, also reacts with mineral acids in the presence of ZnI 2 to give 2-hydroxycarboxylic acid amides. [79] If the ketone 50 is treated with two equivalents of the isocyanide 51 in the presence of BF 3´O Et 2 in nonpolar solvents, the b,g-unsaturated a-oxocarboxylic amide 52 is formed.…”

Section: Mcr Typementioning

confidence: 99%

Multicomponent Reactions with Isocyanides

Dömling

Ugi

2000

Angew. Chem. Int. Ed.

4,000

1,635

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Multicomponent reactions (MCRs) are fundamentally different from two‐component reactions in several aspects. Among the MCRs, those with isocyanides have developed into popular organic‐chemical reactions in the pharmaceutical industry for the preparation of compound libraries of low‐molecular druglike compounds. With a small set of starting materials, very large libraries can be built up within a short time, which can then be used for research on medicinal substances. Due to the intensive research of the last few years, many new backbone types have become accessible. MCRs are also increasingly being employed in the total synthesis of natural products. MCRs and especially MCRs with isocyanides offer many opportunities to attain new reactions and basic structures. However, this requires that the chemist learns the “language” of MCRs, something that this review wishes to stimulate.

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Section: Mcr Typementioning

confidence: 99%

Multicomponent Reactions with Isocyanides

Dömling

Ugi

2000

Angew. Chem. Int. Ed.

4,000

1,635

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“…The reaction of isocyanides with aldehydes mediated by Brønsted or Lewis acids has been developed to afford the corresponding α‐hydroxyamide. However, the nitrilium intermediate is subject to further addition of isocyanide and this often leads to undesired products . Moreover, the cleavage of the Lewis acid from the product is required .…”

Section: Borinic Acid Catalyzed α‐Addition To Isocyanide With Aldehydmentioning

confidence: 99%

Carboxylic Acid Free Novel Isocyanide‐Based Reactions

Soeta

Ukaji

2014

The Chemical Record

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In order to develop a practical method for the construction of drug-like and heterocyclic compounds, we have designed a novel Passerini- or Ugi-type reaction system where a compound (which we write in the general form as Z-X) composed of an electrophilic (Z) and a nucleophilic group (X) could essentially perform the same function as the carboxylic acid. Based on this concept, we have developed the O-silylative Passerini reaction and the borinic acid catalyzed α-addition of isocyanides to aldehydes and water. In addition, we have designed and demonstrated the addition reaction of isocyanides to nitrones in the presence of TMSCl to afford the corresponding 1,2,3,4-tetrahydroisoquinoline-1-carboxyamides. Furthermore, a novel [5 + 1] cycloaddition of isocyanide was explored with C,N-cyclic N'-acyl azomethine imines as a "1,5-dipole" via a strategy involving intramolecular trapping of the isocyanide.

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“…There are almost no limitations in the choice of the oxo component used: both aldehydes and ketones can be utilized. Some sterically hindered and a,b-unsaturated ketones as well as bicyclic extremely hindered ketones such as camphor do not react with isocyanides in a Passerini reaction [47]. Besides ''normal'' C-isocyanides, Me 3 SiCN, which is in an equilibrium with Me 3 SiNC, also reacts with mineral acids in the presence of ZnI 2 to give 2-hydroxy carboxylic acids and amides [48].…”

Section: Passerini Reactionmentioning

confidence: 99%