Synthesis of Pyridin‐2(1<i>H</i>)‐one Derivatives: Temperature‐Dependent Selectivity

Chikhalikar, Sandip; Bhawe, Vijay; Jachak, Madhukar N.; Ghagare, Maruti G.

doi:10.1002/ejoc.201100800

Cited by 6 publications

(3 citation statements)

References 43 publications

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“…To address this problem and as a continuation of our work towards the synthesis of nitrogen containing heterocycles, 27,28 we intended to develop a convenient synthetic approach for the synthesis of new pyrazolo [1,5-a]pyrimidine annulated heterocycles.…”

Section: Introductionmentioning

confidence: 99%

An efficient synthesis of pyrazolo[1,5-a]pyrimidines and evaluation of their antimicrobial activity

et al. 2016

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A series of new pyrazolo[1,5-a]pyrimidine derivatives has been synthesized by using 7-hydrazinyl-5-methylpyrazolo[1,5-a]pyrimidine-3-carbonitrile 1 and 7-amino-5-methylpyrazolo[1,5-a]pyrimidine-3-carbonitrile 2 as precursors. The pyrazolo[3,4-d] pyrimidines 3a-b have been synthesized by a three-step reaction starting with 1. Compound 1 was utilized for the synthesis of dioxopyrrolidindolinylamio-pyrazolo-pyrimidines 4a-b, and dioxoisoindolin-pyrazolo-pyrimidines 4c-d. Also, compounds 4a-d were synthesized using deep eutectic solvents (DES). This method using DES provides several advantages such as benign environment, high yield, scalable and simple work-up procedure. Similarly, the cyclocondensation of 2 with α-acetylγ-butyrolactone afforded pyrazolo-pyrido-pyrimidine 5 and dihydrofuro-pyrido-pyrazolo-pyrimidine 6. All synthesized compounds were screened for antimicrobial activity.

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Section: Introductionmentioning

confidence: 99%

An efficient synthesis of pyrazolo[1,5-a]pyrimidines and evaluation of their antimicrobial activity

et al. 2016

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“…For example, it has been used in the multicomponent preparation of pyrazolopyridin‐2(1 H )‐one derivatives . A similar reagent, 2,2,6‐trimethyl‐4 H ‐1,3‐dioxin‐4‐one, has also been used in the synthesis of pyridin‐2(1 H )‐one derivatives …”

Section: Introductionmentioning

confidence: 99%

Sequential multicomponent synthesis of highly functionalized pyridin-2(1H)-one derivatives

et al. 2016

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Highly functionalized pyridin-2(1H)-one derivatives were synthesized in high yields by a sequential multicomponent reaction. The mechanism involves the Michael addition of Meldrum's acid to 3-formylchromone, followed by the addition of an amine, intramolecular amidation and elimination of acetone. Depending on the temperature used, decarboxylation can occur. The mechanism of this reaction has been proposed based on the by-products obtained when the reaction was performed using poorly reactive amines. The versatility of this approach has been exemplified using various 3-formylchromones and amines. Analogues of Meldrum's acid were also tested, allowing the synthesis of pyridin-2(1H)-one derivatives with various substituents on the aromatic ring.

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“…Prompted with these findings, and our ongoing project to synthesize such nitrogen-containing heterocycles [37][38][39][40], efforts have been taken to develop the convenient synthetic approaches for the synthesis of some new pyrazolo [4,3-d] pyrimidines and their fused heterocycles that might be of pharmacological importance.…”

Section: Introductionmentioning

confidence: 99%

A Convenient Synthesis of New Pyrazolo[4,3‐d]pyrimidines and Their Fused Heterocycles

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Patil

et al. 2013

Journal of Heterocyclic Chem

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A series of some fused heterocycles originated from pyrazolopyrimidines were synthesized using 4‐amino1‐methyl‐3‐propyl‐1H‐pyrazole‐5‐carboxamide as a starting material. The nucleophilic substitution reactions with different amino acids followed by cyclization and Suzuki–Miyaura cross‐coupling reactions with different aryl boronic acids of 7‐chloro‐5‐(4‐chlorophenyl)‐1‐methyl‐3‐propyl‐1H‐pyrazolo[4,3‐d]pyrimidine were performed. Also, the oxidative cyclization reactions of 1‐(5‐(4‐chlorophenyl)‐1‐methyl‐3‐propyl‐1H‐pyrazolo[4,3‐d]pyrimidin‐7‐yl)hydrazine with different aldehydes in the presence of diacetoxy iodobenzene are described. All the synthesized compounds were characterized by analytical and spectroscopic methods.

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Synthesis of Pyridin‐2(1H)‐one Derivatives: Temperature‐Dependent Selectivity

Cited by 6 publications

References 43 publications

An efficient synthesis of pyrazolo[1,5-a]pyrimidines and evaluation of their antimicrobial activity

An efficient synthesis of pyrazolo[1,5-a]pyrimidines and evaluation of their antimicrobial activity

Sequential multicomponent synthesis of highly functionalized pyridin-2(1H)-one derivatives

A Convenient Synthesis of New Pyrazolo[4,3‐d]pyrimidines and Their Fused Heterocycles

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