A convenient synthesis of 4-alkyl-3-benzoylpyrroles from α,β-unsaturated ketones and tosylmethyl isocyanide

Kumar, Kapil; More, Shital S.; Goyal, Sandeep; Gangar, Mukesh; Khatik, Gopal L.; Rawal, Ravindra K.; Nair, Vipin A.

doi:10.1016/j.tetlet.2016.04.056

Cited by 25 publications

(8 citation statements)

References 56 publications

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“…As shown in Scheme 3 , the electron-withdrawing groups may be esters, amides, ketones, nitros, cyanos, aryls, etc. [ 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 , 54 , 55 , 56 , 57 , 58 , 59 , 60 ]. Based on the different types of electron-withdrawing group attached to the alkenes, they are classified and described in order ( Scheme 3 ).…”

Section: Synthesis Of Pyrrole Derivatives By [3+2] Cycloaddition Omentioning

confidence: 99%

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Synthesis of Multi-Substituted Pyrrole Derivatives Through [3+2] Cycloaddition with Tosylmethyl Isocyanides (TosMICs) and Electron-Deficient Compounds

Zhang

2018

Molecules

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Pyrrole and its polysubstituted derivatives are important five-membered heterocyclic compounds, which exist alone or as a core framework in many pharmaceutical and natural product structures, some of which have good biological activities. The Van Leusen [3+2] cycloaddition reaction based on tosylmethyl isocyanides (TosMICs) and electron-deficient compounds as a substrate, which has been continuously developed due to its advantages such as operationally simple, easily available starting materials, and broadly range of substrates, is one of the most convenient methods to synthetize pyrrole heterocycles. In this review, we discuss the different types of two carbon synthons in the Van Leusen pyrrole reaction and give a summary of the progress of these synthesis methods in the past two decades.

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Section: Synthesis Of Pyrrole Derivatives By [3+2] Cycloaddition Omentioning

confidence: 99%

“…Moreover, they found that LiOH·H 2 O gave good yields of the desired product as compared to NaOH and KOH. This might be due to better coordination power of lithium ( Scheme 31 ) [ 50 ].…”

Section: Synthesis Of Pyrrole Derivatives By [3+2] Cycloaddition Omentioning

confidence: 99%

Synthesis of Multi-Substituted Pyrrole Derivatives Through [3+2] Cycloaddition with Tosylmethyl Isocyanides (TosMICs) and Electron-Deficient Compounds

Zhang

2018

Molecules

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“…Generally, a stepwise mechanism rather than a concerted process is proposed in the van Leusen pyrrole synthesis from the [3+2] cycloaddition of electron-deficient olefins with TosMIC [ 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 ]. Thus, on the basis of the related reports [ 43 , 44 , 45 , 46 , 47 , 48 ] and above-stated results, a possible mechanism for the synthesis of 3 was proposed and depicted in Scheme 2 .…”

Section: Resultsmentioning

confidence: 99%

“…Among them, the [3+2] cycloaddition of tosylmethyl isocyanide with electron-deficient olefins, developed by van Leusen et al, is one of the most promising methods [ 12 , 13 , 14 , 15 , 16 , 17 , 18 ]. A wide range of electron-deficient olefins, such as α,β-unsaturated esters, ketones or nitriles, nitroolefins and styrenes, etc., are well tolerated in this reaction [ 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 ]. 3-Methyl-4-nitro-5-alkenylisoxazoles, developed by Adamo et al, are excellent activated olefins, which hold excellent potential for the generation of diversity [ 37 , 38 , 39 , 40 ].…”

Section: Introductionmentioning

confidence: 99%

[3+2] Cycloaddition of Tosylmethyl Isocyanide with Styrylisoxazoles: Facile Access to Polysubstituted 3-(Isoxazol-5-yl)pyrroles

Zhang

2017

Molecules

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A facile access to polysubstituted 3-(isoxazol-5-yl)pyrroles was developed through [3+2] cycloaddition of tosylmethyl isocyanide (TosMIC) and styrylisoxazoles. In the presence of KOH, various styrylisoxazoles reacted smoothly with tosylmethyl isocyanide and analogs to deliver a wide range of 3-(isoxazol-5-yl)pyrroles at ambient temperature. This transformation is operationally simple, high-yielding, and displays broad substrate scope.

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“…Element analyses were performed on a Perkin‐Elmer 240 CHN analyzer. 2‐chloroquinoline‐3‐carbaldehyde 1 , 2‐(4‐phenylpiperazin‐1‐yl)quinolin‐3‐carbaldehyde 2 , 2‐chloromethyl‐5‐aryl‐1,3,4‐oxadiazole, 1‐phenyl‐2‐(triphenylphosphoranylidene)ethanone, and hydroximoyl chloride were prepared using literature reported methods …”

Section: Methodsmentioning

confidence: 99%

Design and synthesis of novel quinoline derivatives bearing oxadiazole, isoxazoline, triazolothiadiazole, triazolothiadiazine, and piperazine moieties

Tang

Peng

Liu

2020

Journal of Heterocyclic Chem

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A new series of 2,3‐disubstituted quinoline derivatives were synthesized from 2‐chloroquinoline‐3‐carbaldehyde. In the reaction sequence, acetanilide was cyclized to give 2‐chloroquinoline‐3‐carbaldehyde 1, which was transformed to 2‐(4‐phenylpiperazin‐1‐yl)quinolin‐3‐carbaldehyde 2 by reaction with 4‐phenylpiperazine in DMF‐containing anhydrous K2CO3; then, compound 2 was oxidized by iodine in methanol, and methyl 2‐(4‐phenylpiperazin‐1‐yl)quinoline‐3‐carboxylate 3 was synthesized. The key intermediate 4, 4‐amino‐5‐[2‐(4‐phenylpiperazin‐1‐yl)quinolin‐3‐yl]‐4H‐1,2,4‐triazole‐3‐thiol, was prepared using the ester 3 by a series of step. Reaction of 5 with various aromatic carboxylic acids or phenacyl bromides yielded 1,2,4‐triazolo[3,4‐b][1,3,4]thiadiazoles 5a‐c and 1,2,4‐triazolo[3,4‐b][1,3,4]thiadiazines 6a‐c, respectively. Moreover, compound 2 condensed with o‐phenylenediamine to give 2‐[2‐(4‐phenylpiperazin‐1‐yl)quinolin‐3‐yl]‐1H‐benzimidazole 7. Interaction of 7 and 2‐chloromethyl‐5‐aryl‐1,3,4‐oxadiazoles in the presence of K2CO3 led to the title compounds 8a‐c. Furthermore, 4,5‐dihydroisoxazoline derivatives 9a‐c were obtained by the reaction of readily accessible starting materials including 2‐(4‐phenylpiperazin‐1‐yl)quinolin‐3‐carbaldehyde 2, 1‐phenyl‐2‐(triphenylphosphoranylidene)ethanone and hydroximoyl chlorides under mild conditions in the presence of Et3N. The hydrazone intermediates 10a‐c were obtained by the condensation of 2 with aroylhydrazides in ethanol, then, refluxing in acetic anhydride yielded 3‐acetyl‐5‐aryl‐2‐[2‐(4‐phenylpiperazin‐1‐yl)quinolin‐3‐yl]‐2,3‐dihydro‐1,3,4‐oxadiazoles 11a‐c. Structures of these compounds were established by their elemental analysis, IR, 1H NMR, and mass spectral data.

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A convenient synthesis of 4-alkyl-3-benzoylpyrroles from α,β-unsaturated ketones and tosylmethyl isocyanide

Cited by 25 publications

References 56 publications

Synthesis of Multi-Substituted Pyrrole Derivatives Through [3+2] Cycloaddition with Tosylmethyl Isocyanides (TosMICs) and Electron-Deficient Compounds

Synthesis of Multi-Substituted Pyrrole Derivatives Through [3+2] Cycloaddition with Tosylmethyl Isocyanides (TosMICs) and Electron-Deficient Compounds

[3+2] Cycloaddition of Tosylmethyl Isocyanide with Styrylisoxazoles: Facile Access to Polysubstituted 3-(Isoxazol-5-yl)pyrroles

Design and synthesis of novel quinoline derivatives bearing oxadiazole, isoxazoline, triazolothiadiazole, triazolothiadiazine, and piperazine moieties

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