One-pot preparation of isocyanides from amines and their multicomponent reactions: crucial role of dehydrating agent and base

Guchhait, Sankar K.; Priyadarshani, Garima; Chaudhary, Vikas; Seladiya, Darshan R.; Shah, Tapan M.; Bhogayta, Nikita P.

doi:10.1039/c3ra40347e

Cited by 29 publications

(25 citation statements)

References 38 publications

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“…The synthesis of six-membered nitrogen-containing heterocycles including, poly-substituted 2,3dihydropyridin-4(1H)-one 335, 1,2,3,4-tetrahydropyridine 336, and pyridine derivatives, was 219 . It was found that the entity of base and dehydrating agent and their amounts played important roles in this procedure.…”

Section: Pyridinementioning

confidence: 99%

Isocyanide-based multicomponent reactions in the synthesis of heterocycles

2016

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Section: Pyridinementioning

confidence: 99%

Isocyanide-based multicomponent reactions in the synthesis of heterocycles

2016

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“…Finally, our study was completed by taking advantage of the mildness of our catalytic conditions to develop a one‐pot procedure for the direct preparation of isocyanide 10 from benzylamine . Among the various possible reagents that are able to dehydrate a formamide, the Burgess reagent was foreseen as being the most compatible upon using DMF as the solvent.…”

Section: Figurementioning

confidence: 99%

Formamide Synthesis through Borinic Acid Catalysed Transamidation under Mild Conditions

Dine

Evans

Rouden

et al. 2016

Chemistry A European J

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A highly efficient and mild transamidation of amides with amines co-catalysed by borinic acid and acetic acid has been reported. A wide range of functionalised formamides was synthesized in excellent yields, including important chiral α-amino acid derivatives, with minor racemisation being observed. Experiments suggested that the reaction rely on a cooperative catalysis involving an enhanced boron-derived Lewis acidity rather than an improved Brønsted acidity of acetic acid.

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“…NFormyl compounds have been used as precursor for the synthesis of formamidines [1], isocyanides [2], aminocarbonylation of aryl halides [3], and as reagents in the classical Vilsmeier formylation reactions [4]. Furthermore, they are valuable intermediates in the construction of various medicinally important compounds such as quinolone antibiotics [5] and cancer chemotherapeutic agents [6].…”

Section: Introductionmentioning

confidence: 99%

Acidic ionic liquid immobilized on nanoporous Na+-montmorillonite as an efficient and reusable catalyst for the formylation of amines and alcohols

2015

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In this work, nanoporous sodium montmorillonite clay (Na ? -MMT) was used as a support for the immobilization of 1-methyl-3-(trimethoxysilylpropyl)-imidazolium hydrogen sulfate. The Na ? -MMT chemical modification ([Na ? -MMT-[pmim]HSO 4 ) was confirmed by a variety of techniques including Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), thermogravimetric analysis (TGA), scanning electron microscopy and potentiometric titration. The catalytic performance of this immobilized acidic ionic liquid was probed for the N-formylation of a variety of amines using formic acid under solvent-free conditions. This reagent is also useful for the formylation of benzylic alcohols. The procedure gave the products in excellent yields in very short reaction times. Also, this catalyst can be reused ten times without loss of its catalytic activity.

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One-pot preparation of isocyanides from amines and their multicomponent reactions: crucial role of dehydrating agent and base

Abstract: One-pot preparation of isocyanides from amines and their multicomponent reactions: crucial role of dehydrating agent and base3

Cited by 29 publications

References 38 publications

Isocyanide-based multicomponent reactions in the synthesis of heterocycles

Isocyanide-based multicomponent reactions in the synthesis of heterocycles

Formamide Synthesis through Borinic Acid Catalysed Transamidation under Mild Conditions

Acidic ionic liquid immobilized on nanoporous Na+-montmorillonite as an efficient and reusable catalyst for the formylation of amines and alcohols

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