Efficient synthesis of dihydropyrido[4,3-d]pyrimidines by microwave-promoted three-component aza-Diels–Alder reaction

Sarmah, Manas M.; Sarma, Rupam; Prajapati, Dipak; Hu, Wenhao

doi:10.1016/j.tetlet.2012.11.018

Cited by 18 publications

(5 citation statements)

References 36 publications

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“…Sarmah et al reported the multi‐component reaction via microwave‐assisted protocol that has been used for synthesizing dihydropyrido[4,3‐ d ]pyrimidine derivatives from 6‐[2(dimethylamino)vinyl]‐1,3‐dimethyluracil that reacts with substituted aldehyde and aromatic amine (Scheme 14). In this series, the Diels‐Alder reaction is an influential strategy and efficient method for obtaining an excellent yield of 70 within a few minutes and 1:1 of p ‐chlorobenzaldehyde and p ‐chloroaniline react to each other at 400 W under a microwave condition without catalyst (Sarmah et al, 2013).…”

Section: Synthetic Methods Of Pyrido[43‐d]pyrimidinesmentioning

confidence: 99%

“…Tetrahydropyrido [4,3-d]pyrimidines Gastric antilesion agents Sanfilippo et al (1992) other at 400 W under a microwave condition without catalyst (Sarmah et al, 2013). Tian et al reported the traditional and efficient method for 80(a-e) synthesis via acid-promoted cyclization of cyanoenamine to afford 2,4-bis-thiomethyl pyrido [4,3-d] pyrimidin-5(6H)-one as a key intermediate, which could allow the independent functionalization of 2 and 4 positions.…”

Section: S C H E M E 1 3 Synthesis Of Substituted Tetrahydropyrido[43...mentioning

confidence: 99%

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Chemistry and biological evaluation of pyrido[4,3‐d]pyrimidines: A review

Yadav

Shah

2022

Chem Biol Drug Des

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The aim of this review is to update the knowledge of different multi‐component reactions that lead to synthesizing of pyrido[4,3‐d]pyrimidines. In this study, the multiple synthetic pathways that are discussed in the synthesis of pyrido[4,3‐d]pyrimidines lead are highlighted. Thus, the developed compounds have been derived from pyridine and pyrimidines fusion or from possible approaches of multistep synthesis reaction versatility. Apart from the synthetic schemes, their biological applications are also comprehended. This review discusses that the pyrido[4,3‐d]pyrimidines have been developed by using new strategies and may be useful to future researchers.

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Section: Synthetic Methods Of Pyrido[43‐d]pyrimidinesmentioning

confidence: 99%

Section: S C H E M E 1 3 Synthesis Of Substituted Tetrahydropyrido[43...mentioning

confidence: 99%

Chemistry and biological evaluation of pyrido[4,3‐d]pyrimidines: A review

Yadav

Shah

2022

Chem Biol Drug Des

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“…This method was eco-friendly, easily separation of catalyst and reduce waste product [7]. [2(dimethylamino)vinyl]-1,3-dimethyluracil reacts with substituted aldehyde and aromatic amine [11]. In this series, the Diels-Alder reaction is an influential strategy and efficient methods for obtaining in excellent yield 14 within few minutes and 1:1 of p-chlorobenzaldehyde and p-chloroaniline reacted with each other at 400W under a microwave condition without catalyst (Scheme 5).…”

Section: Synthetic Pathway For Pyridopyrimidinesmentioning

confidence: 99%

Pyridopyrimidines as Anticancer Agents

Yadav

Shah

2022

ECS Trans.

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The main purpose of this review is to provide an overview of the current knowledge for development of new molecules of pyridopyrimidines by using different multi-component reactions that lead to give effective anticancer agents. Thus, the developed compounds have been derived from pyridine and pyrimidines fusion or from possible isomeric forms of pyridopyrimidine derivatives. They are obtained from different approaches of multistep synthesis reaction such as Tandemaza-witting reaction, annulations, and Biginelli type reactions. Apart from the synthetic schemes, their biological applications with an alternative mechanism of action, such as growth inhibitors by cell cycle arrest, apoptosis, inhibition of angiogenesis, disruption of cell migration, and mutation, are also understood. These receptors and enzymes are responsible for causes of cancer because disruptions of dihydrofolate reductase, tyrosine kinase, cyclin-dependent kinase-4 and 6, and fibroblast growth factor receptor. Among heterocyclic compounds, pyridopyrimidine compounds are privileged structure in medicinal chemistry, especially with FGFR-TK, CDK-4, ABCG-2, Ef-2 kinase, and Type-II pan-RAF kinase inhibitors (Figure 1). The present review illustrates that pyridopyrimidines have been developed by using new strategies and may be utilized for treatment of various cancer.

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“…Prajapati et al [ 34 ] established a microwave‐promoted effective procedure for the construction of dihydropyrido[4,3‐ d ]pyrimidine derivatives in short span of time with decent to exceptional yield. The reaction was optimized from readily available starting materials like 6‐[2‐ (dimethylamino)vinyl]‐1,3‐dimethyl uracil 85 with 4‐chloro benzaldehyde 86 and 4‐chloro aniline 87 under MWI at 400 W using microwave power without catalyst.…”

Section: Synthetic Strategiesmentioning

confidence: 99%

Microwave‐assisted diversified synthesis of pyrimidines: An overview

Kumar

2021

Journal of Heterocyclic Chem

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Pyrimidines and their hybrid molecules have continued to be a favorable area for organic chemists owing to their richness in natural and synthetic compounds with multifarious involvement in pharmaceuticals and polymers and act as ligands. Different novel and greener synthetic protocols were developed in the last decades, but microwave‐assisted synthetic protocols played a significant role in constructing pyrimidine and its derivatives. In this article, we summarized the microwave‐supported strategy for the construction of pyrimidine fused or linked/tethered with other heterocycles, polysubstituted pyrimidines, solid‐supported synthesis of pyrimidines, and ionic liquid‐catalyzed strategies for the synthesis of pyrimidine and its derivatives reported in the last decade. Solid‐supported protocols using resins and ionic liquid‐catalyzed strategies afforded the corresponding products with excellent yield by dual activation. In most of the reports, the microwave‐irradiated approach was compared with conventional/traditional heating and found better in terms of reaction time, yield, atom economy, adherence with green chemistry principles, and reduction in purification wastage. Various authors evaluated the in vitro potential of synthesized pyrimidine derivatives for antimicrobial and antimalarial potential, and found moderate to excellent biological activity.

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Efficient synthesis of dihydropyrido[4,3-d]pyrimidines by microwave-promoted three-component aza-Diels–Alder reaction

Cited by 18 publications

References 36 publications

Chemistry and biological evaluation of pyrido[4,3‐d]pyrimidines: A review

Chemistry and biological evaluation of pyrido[4,3‐d]pyrimidines: A review

Pyridopyrimidines as Anticancer Agents

Microwave‐assisted diversified synthesis of pyrimidines: An overview

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