Synthesis of Highly Substituted 4<i>H</i>-Pyrido[1,2-<i>a</i>]pyrimidines via a One-Pot Three-Component Condensation Reaction

Yang, Kai; Xiang, Jinbao; Bao, Guochen; Dang, Qun; Bai, Xu

doi:10.1021/co400086u

Cited by 24 publications

(14 citation statements)

References 49 publications

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“…Dihydropyrimidinone derivatives 355 have been synthesized from the reaction of ethyl acetoacetate derivatives 352, aldehydes, and thiourea/urea (353, 354) through a Biginelli-type reaction in the presence of acid functionalized ionic liquid derived from Scheme 105 One-pot synthesis of dihydrotetrazolo [1,5-a] . A broad range of aromatic and aliphatic ketones and aldehydes were introduced in this study to know the generality of the reaction and the results were found in good agreement [214].…”

Section: Synthesis Of Pyrimidinesmentioning

confidence: 70%

Transition metal-free one-pot synthesis of nitrogen-containing heterocycles

et al. 2015

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One-pot heterocyclic synthesis is an exciting research area as it can open routes for the development of otherwise complex transformations in organic synthesis. Heterocyclic compounds show wide spectrum of applications in medicinal chemistry, chemical biology, and materials science. These heterocycles can be generated very efficiently through highly economical and viable routes using one-pot synthesis. In particular, the metal-free one-pot synthetic protocols are highly fascinating due to several advantages for the industrial production of heterocyclic frameworks. This comprehensive review is devoted to the transition metal-free one-pot synthesis of nitrogen-containing heterocycles from the period 2010-2013.

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Section: Synthesis Of Pyrimidinesmentioning

confidence: 70%

Transition metal-free one-pot synthesis of nitrogen-containing heterocycles

et al. 2015

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“…Recently, synthesis of 4 H ‐pyrido[1,2‐ a ]pyrimidines using trifluoromethanesulfonic was reported . In this reaction, condensation of 2‐aminopyridines 20 , aldehydes 21 , and ketones or aldehydes 22 in the presence of trifluoromethanesulfonic acid as catalyst was carried out to prepare 4 H ‐pyrido[1,2‐ a ]pyrimidines 23 (Scheme ).…”

Section: The Mcrs Synthesis Of Pyridopyrimidinesmentioning

confidence: 99%

Recent Developments in the MCRs Synthesis of Pyridopyrimidines and Spiro‐Pyridopyrimidines

Mamaghani

Nia

2016

Journal of Heterocyclic Chem

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Because of biological and medicinal properties of pyridopyrimidines, synthesis of these heterocycles has attracted the interest of organic and medicinal chemists. This review focuses on the recent development in the multi‐component synthesis of pyridopyrimidine and spiro‐conjugated pyridopyrimidine systems. The present review describes the literature reports for the period 2000–2015, particularly those that involve the reactions of activated methylene, aldehyde or ketone, and amine in classical and nonclassical conditions.

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“…Pyrido[1,2‐α]pyrimidines are one important class of aza‐bridgehead fused heterocyclic scaffolds that demonstrates a broad range of biological and pharmacological activities such as anticancer, anxiolytic, antioxidant, anticonvulsant, antidepressant and antibacterial activities [26–31] . Recently, we have synthesized a novel pyrido[1,2‐α]pyrimidine derivative, 4‐imino‐4 H ‐pyrido[1,2‐α]pyrimidine‐3‐carbonitrile, and demonstrated its potent PL and ECL for the first time [32] .…”

Section: Introductionmentioning

confidence: 99%

Optimizing the Electrochemiluminescence of Readily Accessible Pyrido[1,2‐α]pyrimidines through “Green” Substituent Regulation

et al. 2021

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Bright and low‐cost emitting organic molecules are very desirable for electrochemiluminescence (ECL). Here, we report a facile one‐step, three‐component reaction of readily available precursors to synthesize pyrido[1,2‐α]pyrimidine derivatives (1–4), all which give off green photoluminescence (PL). In contrast, the electrochemistry and ECL properties of these luminophores are affected by the extent of the conjugation and the nature of the peripheral substituents. Density functional theory (DFT) calculations identified the aromatic chain substitution could extend the conjugation of pyrido[1,2‐α]pyrimidine core and stabilize the electrogenerated radicals required for generation of an excited state, affording pyrido[1,2‐α]pyrimidine 3 the highest ECL activity among the studied samples. ECL in annihilation route confirmed weak emission, but great improvement was made using oxidizing co‐reactant species (benzoate radical from benzoyl peroxide, BPO) with an efficiency of 43 % relative to that of Ru(bpy)3(PF6)2. The pyrido[1,2‐α]pyrimidine 3/BPO system is more robust than those of reducing co‐reactant species [tri‐n‐propylamine radical or 2‐(dibutylamino) ethanol radical] and is one of the highest among the reported organic electrochemiluminophores. ECL spectroscopy revealed that the monomeric excited states were the main species to emit light. Their straightforward, one‐step, green synthesis, and their structure tunability represent significant advantages in the development of readily accessible dyes for PL and especially ECL applications.

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Synthesis of Highly Substituted 4H-Pyrido[1,2-a]pyrimidines via a One-Pot Three-Component Condensation Reaction

Abstract: A one-pot three-component reaction, involving condensation of 2-aminopyridines, aldehydes, and ketones/aldehydes under trifluoromethanesulfonic acid catalysis, provides rapid access to highly substituted novel 4H-pyrido[1,2-a]pyrimidines.

Cited by 24 publications

References 49 publications

Transition metal-free one-pot synthesis of nitrogen-containing heterocycles

Transition metal-free one-pot synthesis of nitrogen-containing heterocycles

Recent Developments in the MCRs Synthesis of Pyridopyrimidines and Spiro‐Pyridopyrimidines

Optimizing the Electrochemiluminescence of Readily Accessible Pyrido[1,2‐α]pyrimidines through “Green” Substituent Regulation

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