Propylphosphonic anhydride (T3P®) mediated synthesis of 3-oxoisoindoline-1-carboxamides from 2-formylbenzoic acid, amines, and isocyanides. Preparation of isoindolinone alkaloids

Varga, Valentina; Milen, Mátyás; Ábrányi‐Balogh, Péter

doi:10.1016/j.tetlet.2018.08.063

Cited by 15 publications

(7 citation statements)

References 25 publications

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“…[54,56] These methodologies enable the synthesis of symmetric or asymmetric thioureas from the isothiocyanate precursor isocyanides and the isolation of the pure products by a simple filtration. In continuation of our interest in multicomponent reactions [58][59][60] and reactions involving elemental sulfur [54][55][56]61] we have aimed to further elaborate the application of aqueous polysulfide solutions. Herein we present the multicomponent one-pot synthesis of diverse 2-iminothiazolines and 2-aminothiazoles starting from isocyanides, sulfur, amines, and 2'-bromoacetophenones (Scheme 1, eq.…”

Section: Introductionmentioning

confidence: 99%

Convenient Multicomponent One‐Pot Synthesis of 2‐Iminothiazolines and 2‐Aminothiazoles Using Elemental Sulfur Under Aqueous Conditions

et al. 2021

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Dedicated to professor Ferenc Fülöp on the occasion of his 70th birthday.Herein, we present a novel one-pot aqueous reaction for the synthesis of 2-iminothiazolines and 2-aminothiazoles using isocyanides, amines, sulfur, and 2'-bromoacetophenones. The three-component preparation of thioureas is followed by the one-pot cyclization leading to the heterocyclic product. This efficient and mild procedure features excellent step-and atomeconomy and enables the chromatography-free preparation of diversely substituted 2-iminothiazoline and 2-aminothiazole derivatives.

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Section: Introductionmentioning

confidence: 99%

Convenient Multicomponent One‐Pot Synthesis of 2‐Iminothiazolines and 2‐Aminothiazoles Using Elemental Sulfur Under Aqueous Conditions

et al. 2021

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“…Notably, its features of accelerating reactions and simplifying the isolation of the products are regarded as main advantages of its application in organic reactions. [47][48][49][50] In continuation of our interest in green chemistry, [51] multicompo-nent reactions [52][53][54] and reactions involving sulfur [19,55] we aimed to develop an environmentally friendly synthesis for diverse thioureas, including challenging biaryl derivatives. We envi-sioned the preparation of aqueous solutions of polysulfide anions to use it as a novel agent for the incorporation of sulfur atom.…”

Section: Introductionmentioning

confidence: 99%

Chromatography‐Free Multicomponent Synthesis of Thioureas Enabled by Aqueous Solution of Elemental Sulfur

et al. 2020

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The development of a new three-component chromatographyfree reaction of isocyanides, amines and elemental sulfur allowed us the straightforward synthesis of thioureas in water. Considering a large pool of organic and inorganic bases, we first optimized the preparation of aqueous polysulfide solution from elemental sulfur. Using polysulfide solution, we were able to omit the otherwise mandatory chromatography, and to isolate the crystalline products directly from the reaction mixture by a simple filtration, retaining the sulfur in the solution phase. A wide range of thioureas synthesized in this way confirmed the reasonable substrate and functional group tolerance of our protocol.

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“…More recently, a novel three-component method has been published starting from readily available amines and sodium bromodifluoracetate [84], but this synthetic route provides halogenated waste, as well. As a continuation of our interest in the development of multicomponent reactions [85–87] and reactions involving sulfur [88], herein, we describe a novel synthesis of O -thiocarbamates and dithiocarbamates via a three-component reaction of elemental sulfur, isocyanides and alcohols or thiols (Scheme 1). Moreover, during the investigation of the reaction mechanism, we have identified and improved a catalyst-free method for the preparation of isothiocyanates.…”

Section: Introductionmentioning

confidence: 99%

A novel three-component reaction between isocyanides, alcohols or thiols and elemental sulfur: a mild, catalyst-free approach towards O-thiocarbamates and dithiocarbamates

Németh¹,

Keserü²,

Ábrányi‐Balogh³

2019

Beilstein J. Org. Chem.

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A new multicomponent reaction has been developed between isocyanides, sulfur and alcohols or thiols under mild reaction conditions to afford O-thiocarbamates and dithiocarbamates in moderate to good yields. The one-pot reaction cascade involves the formation of an isothiocyanate intermediate, thus a catalyst-free synthesis of isothiocyanates, as valuable building blocks from isocyanides and sulfur is proposed, as well. The synthetic procedure suits the demand of a modern organic chemist, as it tolerates a wide range of functional groups, it is atom economic and easily scalable.

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Propylphosphonic anhydride (T3P®) mediated synthesis of 3-oxoisoindoline-1-carboxamides from 2-formylbenzoic acid, amines, and isocyanides. Preparation of isoindolinone alkaloids

Cited by 15 publications

References 25 publications

Convenient Multicomponent One‐Pot Synthesis of 2‐Iminothiazolines and 2‐Aminothiazoles Using Elemental Sulfur Under Aqueous Conditions

Convenient Multicomponent One‐Pot Synthesis of 2‐Iminothiazolines and 2‐Aminothiazoles Using Elemental Sulfur Under Aqueous Conditions

Chromatography‐Free Multicomponent Synthesis of Thioureas Enabled by Aqueous Solution of Elemental Sulfur

A novel three-component reaction between isocyanides, alcohols or thiols and elemental sulfur: a mild, catalyst-free approach towards O-thiocarbamates and dithiocarbamates

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