Synthesis of New [1,2,4]Triazolo[1,5‐<i>a</i>]pyrimidine Derivatives: Reactivity of 3‐Amino[1,2,4]triazole towards Enaminonitriles and Enaminones

Alnajjar, Abdulaziz; Abdelkhalik, Mervat Mohammed; Raslan, Mohamed A.; Ibraheem, Solwan Maher; Sadek, Kamal Usef

doi:10.1002/jhet.3222

Cited by 14 publications

(8 citation statements)

References 23 publications

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“…The synthesis of 7‐substituted‐[1,2,4]‐triazolo[1,5‐ a ]pyrimidine 44 a – b (40–44 %) and 6‐substituted‐[1,2,4]‐triazolo[1,5‐ a ]pyrimidine‐7‐amine 45 (78‐87 %) derivatives via reaction of 3‐amino‐[1,2,4]‐triazole with enaminonitriles and enaminones (Scheme 26) using potassium carbonate in DMF was reported by Alnajjar et al [36] …”

Section: Triazolopyrimidine Synthesismentioning

confidence: 94%

Different Synthetic Methods for the Preparation of Triazolopyrimidines and their Biological Profile

et al. 2023

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One or more nitrogen‐containing molecules constitute an important class of heterocyclic compounds in organic synthesis, due to their reactivity and their presence in many molecules of natural, human or plant origin. These nitrogenous heterocycles play an essential role in various scientific domains, whether they are chemical, biological or pharmacological. N‐heterocycles are the privileged source of many research topics developed by several groups of researchers. Thus, different methods have been developed to access these heterocyclic compounds with nitrogenous rings, such as triazolopyrimidines. In this review, a bibliographic study summarizing the pharmacological importance of the triazolo[1,5‐a]pyrimidine ring, the different synthesis routes of these derivatives as well as their reactivity was reported.

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Section: Triazolopyrimidine Synthesismentioning

confidence: 94%

Different Synthetic Methods for the Preparation of Triazolopyrimidines and their Biological Profile

et al. 2023

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“…blended 1 H ‐1,2,4‐triazole‐3,5‐diamine ( R19 ) and 1‐(4‐bromophenyl)butane‐1,3‐dione to obtain 7‐(4‐bromophenyl)‐5‐methyl‐[1,2,4]triazolo[1,5‐ a ]pyrimidin‐2‐amine ( P19 ) under reflux conditions (route‐19) [37] . Alnajjar and co‐workers have attained the target molecule P20 (7‐amino‐5‐phenyl‐4,5‐dihydro‐[1,2,4]triazolo[1,5‐ a ]pyrimidine‐6‐carbonitrile) by treating 1 H ‐1,2,4‐triazol‐5‐amine ( R20 ) with 2‐benzylidenemalononitrile under basic conditions (route‐20) [38] . Loubidi et al.…”

Section: Synthetic Methodologies For [124]triazolo[15‐a]pyrimidine Sc...mentioning

confidence: 99%

“…[37] Alnajjar and co-workers have attained the target molecule P20 (7-amino-5-phenyl-4,5-dihydro- [1,2,4]triazolo [1,5-a]pyrimidine-6-carbonitrile) by treating 1H-1,2,4-triazol-5-amine (R20) with 2-benzylidenemalononitrile under basic conditions (route-20). [38] ). [39]…”

Section: Introductionmentioning

confidence: 99%

An Overview on Synthetic and Medicinal Perspectives of [1,2,4]Triazolo[1,5‐a]pyrimidine Scaffold

Merugu

Cherukupalli

Karpoormath

2022

Chemistry & Biodiversity

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Triazolo[1,pyrimidine is an important heterocyclic scaffold known to have a wide range of pharmacological activities such as anticancer, antimicrobial, anti-tubercular, CB 2 cannabinoid agonists, feticide, and adenosine antagonists. Several clinical trials and marketed drugs such as Trapidil, Essramycin, Pyroxsulam, DSM-265, Flumetsulam, GNF-6702, and Cevipabulin indicate the potential of [1,2,4]triazolo[1,5-a]pyrimidine moiety with various functional groups in medicinal chemistry. Herein, we represent a concise report focusing on the synthetic strategies used for diversely substituted [1,2,4]triazolo [1,5-a]pyrimidine analogs and their pharmacological applications. To the best of our knowledge, since 1980, we are the first to write a review on this emerging scaffold, which reveals the synthetic strategies, and pharmacological activities of differently substituted [1,2,4]triazolo[1,5-a]pyrimidine with special emphasis on structure-activity relationship studies.

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“…Triazolopyrimidines and tetrahydroquinolines were synthesized by using numerous approaches and catalysts such as thiamine hydrochloride (VB 1 ) 23 , Nafion-H 24 , phthalhydrazide-MCM-41 (P-MCM-41) 25 , boric acid under aqueous micellar medium 26 , [DABCO](SO 3 H) 2 Cl 2 and [DABCO](HSO 3 ) 2 (HSO 4 ) 2 27 , DBU 28 , microwave irradiation 29 , etc. [30][31][32][33][34][35][36][37][38][39] .…”

Section: Synthesismentioning

confidence: 99%

Synthesis of pyrimidine-6-carbonitriles, pyrimidin-5-ones, and tetrahydroquinoline-3-carbonitriles by new superb oxovanadium(V)-[5,10,15,20-tetrakis(pyridinium)-porphyrinato]-tetra(tricyanomethanide) catalyst via anomeric based oxidation

Dashteh

Makhdoomi

Baghery

et al. 2022

Sci Rep

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Oxovanadium(V)-[5,10,15,20-tetrakis(pyridinium)-porphyrinato]-tetra(tricyanomethanide) [(VO)TPP][(TCM)4] was designed, synthesized and characterized by various techniques such as FT-IR, EDX, SEM equipped with EDX mappings, CHN elemental analysis, ICP-OES, XRD, SEM, TEM, TGA, DTA, DRS, Kubelka–Munk function (Tauc’s plot), and UV–Vis analyses. Then, [(VO)TPP][(TCM)4] was used as a benign and expedient catalyst for the synthesis of numerous heterocyclic compounds such as 5-amino-7-(aryl)-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitriles, 5-amino-7-(aryl)-[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitriles, 7-(aryl)-7,12-dihydro-5H-isochromeno[4,3-d][1,2,4]triazolo[1,5-a]pyrimidin-5-ones, and 4-(aryl)-2-(1H-indol-3-yl)-5,6,7,8-tetrahydroquinoline-3-carbonitriles under solvent-free conditions at 100 °C via a cooperative geminal-vinylogous anomeric based oxidation.

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Synthesis of New [1,2,4]Triazolo[1,5‐a]pyrimidine Derivatives: Reactivity of 3‐Amino[1,2,4]triazole towards Enaminonitriles and Enaminones

Cited by 14 publications

References 23 publications

Different Synthetic Methods for the Preparation of Triazolopyrimidines and their Biological Profile

Different Synthetic Methods for the Preparation of Triazolopyrimidines and their Biological Profile

An Overview on Synthetic and Medicinal Perspectives of [1,2,4]Triazolo[1,5‐a]pyrimidine Scaffold

Synthesis of pyrimidine-6-carbonitriles, pyrimidin-5-ones, and tetrahydroquinoline-3-carbonitriles by new superb oxovanadium(V)-[5,10,15,20-tetrakis(pyridinium)-porphyrinato]-tetra(tricyanomethanide) catalyst via anomeric based oxidation

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