Facile access to α-acyloxyamides via epoxide rearrangement/three-component domino reaction catalyzed by indium(III) chloride

Kadari, Lingaswamy; Krishna, Palakodety Radha; Prapurna, Y. Lakshmi

doi:10.1080/00397911.2016.1201511

Cited by 10 publications

(6 citation statements)

References 14 publications

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“…High-resolution mass spectra were collected by an Agilent 1290-6530 Q-TOF mass spectrometer. The products 4a , 4k , 4l , 4m , and 4n have been reported in the literature studies. − …”

Section: Methodsmentioning

confidence: 99%

Microdroplet Chemistry Accelerating a Three-Component Passerini Reaction for α-Acyloxy Carboxamide Synthesis

Cheng

et al. 2023

J. Org. Chem.

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α-Acyloxy carboxamides are important multifunctional natural products that show bioactive and pharmacological activities. Traditional three-component Passerini reactions among isocyanates, aldehydes/ketones, and carboxylic acids for affording α-acyloxy carboxamides suffer from several drawbacks such as long reaction time, high reaction temperature, special reaction devices, etc. Herein, we developed a high-efficiency microdroplet method for accelerating the Passerini reactions by 3 orders of magnitude by comparing with the rate constants in bulk, achieving high-yield and gram-scale (scaling up to 1.91 g for 1 h collection) synthesis of αacyloxy carboxamides at near room temperature. The Passerini microdroplet method shows a wide scope for a variety of benzoic acids, aryl aldehydes, and isocyanates. Moreover, the Passerini reaction was poorly conducted in aqueous microdroplets but well accelerated in acetonitrile microdroplets with at least 230 times efficiency than on-water Passerini reactions. All results proved it an attractive alternative to classic organic synthesis for the construction of α-acyloxy carboxamides and derivatives.

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“…High-resolution mass spectra were collected by an Agilent 1290-6530 Q-TOF mass spectrometer. The products 4a , 4k , 4l , 4m , and 4n have been reported in the literature studies. − …”

Section: Methodsmentioning

confidence: 99%

Microdroplet Chemistry Accelerating a Three-Component Passerini Reaction for α-Acyloxy Carboxamide Synthesis

Cheng

et al. 2023

J. Org. Chem.

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“…Mechanistically, at the first step reaction between com- In 2016, Prapurna group demonstrated [43] synthesis of αacyloxyamides 42 through Passerini reaction with various electrophilic epoxides. This is a one-pot three component strategy using epoxide 39, p-toluenesulfonylmethyl isocyanide (TosMIC) 40 and benzoic acid 41 catalyzed by InCl 3 (Scheme 11).…”

Section: Mrityunjoymentioning

confidence: 99%

Recent Advances of Indium(III) Chloride Catalyzed Reactions in Organic Synthesis

Datta

2021

ChemistrySelect

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This review summarizes recent advances of indium trichloride catalyzed synthesis of different organic compounds. It is obvious that InCl3 co‐ordinates with C−C and/or C‐heteroatom multiple bonds and thereby makes them very prone to nucleophilic attack to form a new bond. This Lewis acid catalyst also activates oxiranes to produce aldehydes. Multicomponent synthesis including C−C bond formation reaction and construction of N, O and S‐containing heterocycles are discussed in organic solvents as well as in water. This article highlights recent developments and application of indium(III) chloride as a catalyst in organic synthesis from 2015 to 2020. The mechanism of few important reactions is discussed in detail which will be very useful for the readers.

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“…Starting from aryl or alkyl epoxides, a small library of α-acyloxyamides (11 examples) was generated in very good to excellent yields, under short reaction times, showcasing the versatility of this methodology (Scheme 3). [19] Scheme 3. InCl 3 applied as catalyst in an epoxide-based Passerini reaction (including insights on the mechanism of the in situ aldehyde formation).…”

Section: Isocyanide-based Mcrsmentioning

confidence: 99%

“…Briefly, the catalyst indium(III) chloride (30 mol‐%) promotes, more efficiently than other Lewis acids (FeCl 3 , RuCl 3, or CuI), the epoxide rearrangement into the corresponding aldehyde in situ , which further undergoes the Passerini MCR. Starting from aryl or alkyl epoxides, a small library of α‐acyloxyamides (11 examples) was generated in very good to excellent yields, under short reaction times, showcasing the versatility of this methodology (Scheme ) …”

Section: Introductionmentioning

confidence: 99%

A Decade of Indium‐Catalyzed Multicomponent Reactions (MCRs)

2020

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In the context of synthetic chemistry, Indium is one of the least explored elements of the notorious group 13 of the periodic table and has not attracted quite the same amount of attention as its fellow members, Aluminium and Boron, which have shown unprecedented synthetic applications for more than half a century. Nonetheless, Indium has emerged in recent years as a very valuable catalyst for multicomponent reactions. From the use of indium powder or easily accessible and cheap indium salts to more complex indium‐based metal‐organic frameworks or nanoparticles, a plethora of applications has been described throughout this last decade, showcasing not only the versatility of indium catalysis but also how much there is still to be explored. In the aftermath of the international year of the periodic table of the chemical elements in 2019, we navigated through the large inventory of multicomponent reactions (MCRs) to encounter the types of useful reactions leading to important target compounds (many of which are biologically active) catalyzed by this d‐block post‐transition metal.

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Facile access to α-acyloxyamides via epoxide rearrangement/three-component domino reaction catalyzed by indium(III) chloride

Cited by 10 publications

References 14 publications

Microdroplet Chemistry Accelerating a Three-Component Passerini Reaction for α-Acyloxy Carboxamide Synthesis

Microdroplet Chemistry Accelerating a Three-Component Passerini Reaction for α-Acyloxy Carboxamide Synthesis

Recent Advances of Indium(III) Chloride Catalyzed Reactions in Organic Synthesis

A Decade of Indium‐Catalyzed Multicomponent Reactions (MCRs)

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