☆ 4.7 Article

Access to Pyridyl-Substituted 1,3,5-Triazines from 4H-Pyrido[1,3]oxazin-4-ones via a Cyclocondensation Process

JOURNAL OF ORGANIC CHEMISTRY (2014)

期刊

JOURNAL OF ORGANIC CHEMISTRY

卷 79, 期 14, 页码 6579-6589

出版社

AMER CHEMICAL SOC

DOI: 10.1021/jo5010668

关键词

-

类别

Chemistry, Organic

资金

analytical sciences department of Sanofi RD, France
CNRS
UPMC

向作者/读者索取更多资源

Protocol

Reagent

摘要

Pyridyl-substituted 1,3,5-triazines were synthesized in good to excellent yields via an unprecedented one-step cyclocondensation of 4H-pyrido[1,3]oxazin-4-ones with amidines at room temperature or under microwave irradiations. The broad applicability was demonstrated by 33 examples with a variety of amidines and three different 4H-pyrido[1,3]oxazin-4-one chemical series. In addition, a one-pot process from 4H-pyrido[1,3]oxazin-4-one precursors (imide sodium salts) was developed and led to the desired triazines compounds, thus allowing a one-step economy in their global synthetic preparation. This approach provides rapid access to pyridyl (or pyridone)-substituted 1,3,5-triazines with high potential in various fields of application.

作者

我是这篇论文的作者

点击您的名字以认领此论文并将其添加到您的个人资料中。

评论

主要评分

4.7

评分不足

次要评分

新颖性

-

重要性

-

科学严谨性

-

评价这篇论文

推荐

Article Chemistry, Multidisciplinary

Pd-Catalyzed Carbonylative Synthesis of 4H-Benzo[d][1,3]Oxazin-4-Ones Using Benzene-1,3,5-Triyl Triformate as the CO Source

Yan Zheng, Mengke Dong, Erdong Qu, Jin Bai, Xiao-Feng Wu, Wanfang Li

Summary: A facile synthesis of 4H-benzo[d][1,3]oxazin-4-one derivatives was developed by Pd-catalyzed carbonylative cross-coupling, which does not require toxic and flammable CO gas and tolerates a wide scope of functional groups. Remarkably, this method can be used to construct natural products and drugs containing 4H-benzo[d][1,3]oxazin-4-one structures.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

添加到收藏夹

Article Chemistry, Organic

Difluorocarbene-enabled access to 1,3-oxazin-6-ones from enamides

Shuai Wang, Xin Li, Shengnan Jin, Kang Liu, Cong Dong, Jianke Su, Qiuling Song

Summary: In this study, an efficient and general synthesis method for constructing 1,3-oxazin-6-ones was reported. The method features high efficiency and chemoselectivity, using difluorocarbene as a carbonyl provider. It offers readily available starting materials, valuable products, good functional group tolerance, and simple operation.

ORGANIC CHEMISTRY FRONTIERS (2022)

添加到收藏夹

Article Biochemistry & Molecular Biology

Synthesis and biological evaluation of 4H-benzo[e][1,3]oxazin-4-ones analogues of TGX-221 as inhibitors of PI3Kβ

Ehtesham U. R. Mohammed, Zoe J. Porter, Ian G. Jennings, Jasim M. A. Al-Rawi, Philip E. Thompson, Michael J. Angove

Summary: A novel series of TGX-221 analogues were synthesized by replacing the 4H-pyrido[1,2-a] pyrimidin-4-one scaffold with a 4H-benzo[e][1,3]oxazin-4-one scaffold. The analogues with an -CH(CH3) NH- linker demonstrated comparable activity to TGX-221 analogues, supported by comparative structure-activity relationship analysis. The analogues containing an -CH(CH3)O- linker exhibited lower activity but still displayed useful structure-activity relationship, including a preferred o-methyl substitution.

BIOORGANIC & MEDICINAL CHEMISTRY (2022)

添加到收藏夹

Article Chemistry, Organic

Divergent Synthesis of α-(1,3,5-Triazinylthio)-ketones and Thiazolo[3,2-a][1,3,5]triazines from 1,3-Dicarbonyl compounds or Chalcones with 1,3,5-Triazine-2-thiols

Pengzhen Zhong, Cheng Zhang, Yue Li, Chengwu Su, Chen Zhang, Dong-Mei Cui

Summary: An efficient method for the synthesis of alpha-(1,3,5-triazinylthio)-ketones from 1,3-dicarbonyl compounds with 1,3,5-triazine-2-thiols has been developed. The reaction involves C-C bond cleavage and C-S bond reconstruction of 1,3-dicarbonyl compounds, and can tolerate beta-keto esters, beta-keto amides, and 1,3-diones. In addition, the annulation of 1,3,5-triazine-2-thiols with chalcones has been achieved for the synthesis of thiazolo-[3,2-a]-[1,3,5]-triazines in moderate to good yields, and with a broad functional group tolerance.

JOURNAL OF ORGANIC CHEMISTRY (2023)

添加到收藏夹

Article Chemistry, Multidisciplinary

Silver-Mediated Cascade Synthesis of Functionalized 1,4-dihydro-2H-Benzo-1,3-Oxazin-2-Ones from Carbon Dioxide

Xuetong Li, Jordi Benet-Buchholz, Eduardo C. Escudero-Adan, Arjan W. Kleij

Summary: A conceptually novel catalytic domino approach is presented for the synthesis of highly functional 1,4-dihydro-2H-1,3-benzoxazine-2-one derivatives. The chemoselectivity is achieved through a proper design of the precursor and the use of Thorpe-Ingold effects. The synthetic diversity of these CO2-based heterocycles is demonstrated, and an unusual ring-expansion sequence is observed from an alpha-alkylidene, five-membered cyclic carbonate to a six-membered cyclic carbamate by N-induced isomerization.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2023)

添加到收藏夹

Article Biochemistry & Molecular Biology

Microwave-Assisted Sequential One-Pot Synthesis of 8-Substituted Pyrazolo[1,5-a][1,3,5]triazines

Jonathan Elie, Corinne Fruit, Thierry Besson

Summary: This paper describes a convenient sequential one-pot approach for the synthesis of a series of 14 pyrazolo[1,5-a][1,3,5]triazines, with advantages in terms of yields, reaction times, and convenient gram scale synthesis compared to traditional methods. The combination of efficient heating using dielectric microwave heating and sequential one-pot reactions eliminates the need for laborious work-up and purification of intermediate compounds, allowing for sustainable synthesis processes.

MOLECULES (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Regioselective C(sp2)3-H thiocyanation of substituted 4H-pyrido[1,2-a]pyrimidin-4-ones and its derivatizations

Sanjay Roy, Prasanjit Ghosh, Shibaji Ghosh, Samir K. Mondal, Anirban Mandal, Sajal Das

Summary: In this study, the C(sp(2))-H thiocyanation of substituted 4H-pyrido[1,2-a]pyrimidin-4-ones mediated by K2S2O8 without a metal catalyst was demonstrated for the first time. This unique approach exhibited a broad substrate scope, excellent functional group tolerance, and substitution patterns, leading to the synthesis of thiocyanated scaffolds with high yields and exclusive regioselectivity. Mechanistic investigations were conducted to gain a better understanding of the reaction pathway. Furthermore, the synthetic utility of this protocol was showcased through the construction of biologically relevant analogues.

CHEMISTRYSELECT (2023)

添加到收藏夹

Article Chemistry, Multidisciplinary

Metal free C-3 chalcogenation (sulfenylation and selenylation) of 4H-pyrido[1,2-a]pyrimidin-4-ones

Prasanjit Ghosh, Gautam Chhetri, Sajal Das

Summary: An expeditious metal-free synthesis method has been developed for synthesizing diverse 3-ArS/ArSe derivatives with high yields (up to 95%) of 4H-pyrido[1,2-a]pyrimidin-4-one. This operationally simple reaction, conducted under mild conditions, can be scaled up to gram quantities and shows broad functional group tolerance. Preliminary experimental investigations suggest a radical mechanistic pathway for these transformations.

RSC ADVANCES (2021)

添加到收藏夹

Article Chemistry, Organic

Photoinduced Regioselective Chalcogenation and Thiocyanation of 4H-Pyrido[1,2-a] pyrimidin-4-ones Under Benign Conditions

Abhinay S. Chillal, Rajesh T. Bhawale, Umesh A. Kshirsagar

Summary: A lenient approach for regioselective C3-H chalcogenation and thiocyanation of 4H-pyrido[1,2-a] pyrimidin-4-ones is developed using visible light photocatalysis. This method provides a wide range of functionalized derivatives with moderate to high yields. The protocol utilizes visible light as an environmentally friendly energy source, cost-effective oxidant, and easily obtainable dichalcogenides for selective C-H chalcogenation at room temperature. Additionally, a regioselective thiocyanation method for 4H-pyrido[1,2-a] pyrimidin-4-ones is also developed. Mechanistic pathways for these transformations are proposed based on light on/off and Stern-Volmer studies, as well as quantum yield calculations.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2023)

添加到收藏夹

Article Chemistry, Multidisciplinary

Electrochemical Oxidative Selenation of 4H-Pyrido-[1,2-a]-pyrimidin-4-ones with Diorganyldiselenides

Jinyang Chen, Yao Xiao, Xianhui You, Shiqi Li, Yuwei Fu, Yuejun Ouyang

Summary: An environmentally friendly protocol for the synthesis of C-3-selenylated 4H-pyrido[1,2-a]pyrimidin-4-ones was developed via electrochemical oxidation and iodide-catalyzed selenation. The reaction proceeds efficiently with 10 mol % of KI as catalyst and electrolyte, giving the desired products in good to excellent yields without the use of excess oxidant or iodinated reagents.

CHEMISTRYSELECT (2023)

添加到收藏夹

Article Chemistry, Organic

One-Pot Synthesis of 3-Substituted 4H-Quinolizin-4-ones via Alkyne Substrate Control Strategy

Ji-Wang Fang, Fang-jie Liao, Yang Qian, Chao-Chen Dong, Li-Jin Xu, Han-Yuan Gong

Summary: Three-substituted 4H-quinolizin-4-ones were synthesized with good selectivity and high efficiency using a facile method based on alkyne substrate control. The reaction has a broad substrate scope (20 examples, up to 93% yield) and is easy to scale up. The strategy of alkyne substrate control could be further expanded for more complex structures.

JOURNAL OF ORGANIC CHEMISTRY (2021)

添加到收藏夹

Article Chemistry, Organic

Catalyst- and Oxidant-Free Electrochemical Regioselective Halogenation and Trifluoromethylation of 4H-Pyrido[1,2-a]pyrimidin-4-ones

Meiyun Su, Lina Guo, Peiyu Mao, Meng Xiao, Wenjie Liu, Shaohua Wang

Summary: The catalyst-free electrochemical halogenation and trifluoromethylation of 4H-pyrido[1,2-a]pyrimidin-4-ones was successfully achieved under external-oxidant-free conditions. This strategy provides an easy and green approach for the synthesis of functionalized new 4H-pyrido[1,2-a]pyrimidin-4-one derivatives with broad scope, good functional group tolerance, and high regioselectivity.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2023)

添加到收藏夹

Article Chemistry, Organic

Synthesis of Tetrahydro-4H-pyrido[1,2-b]isoquinolin-4-ones from Ugi 4-CR-Derived Dihydroisoquinoline-Xanthates

Yoarhy A. Amador-Sanchez, Pedro Lopez-Mendoza, Marco Mijangos, Luis D. Miranda

Summary: This synthesis protocol efficiently produces poly-functionalized compounds through a series of reactions.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Synthesis and Reactions of Trifluoromethyl-Substituted 1,3,5-Triazines

Woohyung Jeon, Ramil Baiazitov, Matteo Chierchia, Kyle Niederer, Hongyu Ren, Young-Choon Moon, Bradley B. Gilbert

Summary: This article reports a simple synthetic method for preparing various di- and trifluoromethyl-s-triazines from readily available starting materials. Trichloromethyl-substituted triazine electrophiles were obtained in good yield and reacted with amine nucleophiles to afford aminotriazine products in good to excellent yield. The nucleophilic aromatic substitution reaction showed broad scope, smoothly proceeding with both aromatic and aliphatic amines in the presence of non-participating functional groups, and requiring only a catalytic amount of 4-DMAP without stoichiometric base.

HELVETICA CHIMICA ACTA (2023)

添加到收藏夹

Article Chemistry, Organic

Stannyl radical-mediated synthesis of 6H-1,3-oxazin-6-ones from 2-acyloxyazirines or whether free radicals can open the azirine ring?

Anastasiya Agafonova, Pavel A. Sakharov, Ilia A. Smetanin, Nikolai Rostovskii, Alexander F. Khlebnikov, Mikhail S. Novikov

Summary: A fundamentally new radical cascade reaction of 2-acyloxyazirines provides a one-step method for the preparation of 5-hydroxy-6H-1,3-oxazin-6-ones. The reaction can be applied to various 2-acyloxy-substituted methyl azirine-2-carboxylates, with the volume of the acyloxy substituent influencing the formation of a side product. Additionally, the hydroxyl group in the resulting product can be easily replaced with different groups through palladium-catalyzed cross-coupling reactions.

ORGANIC CHEMISTRY FRONTIERS (2022)

添加到收藏夹

Review Chemistry, Organic

Heteroaromatic Rings of the Future': Exploration of Unconquered Chemical Space

Kevin Passador, Serge Thorimbert, Candice Botuha

SYNTHESIS-STUTTGART (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

A Bis-ChelatingON∧O/NN∧Ligand for the Synthesis of Heterobimetallic Platinum(II)/Rhenium(I) Complexes: Tools for the Optimization of a New Class of Platinum(II) Anticancer Agents

Benoit Bertrand, Candice Botuha, Jeremy Forte, Heloise Dossmann, Michele Salmain

CHEMISTRY-A EUROPEAN JOURNAL (2020)

添加到收藏夹

Article Chemistry, Organic

Synthetic Strategy Studies for a Concise Access to Functionalized Pyrano[4,3-b]pyridin-7-ones: An Entry to Semi-Rigid Analogs of Antihistamines

Anissa Beghennou, Kevin Passador, Anthony Passador, Vincent Corce, Serge Thorimbert, Candice Botuha

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2020)

添加到收藏夹

Article Chemistry, Inorganic & Nuclear

Pincer-Based Heterobimetallic Pt(II)/Ru(II), Pt(II)/Ir(III), and Pt(II)/Cu(I) Complexes: Synthesis and Evaluation of Antiproliferative Properties

Benoit Bertrand, Geoffrey Gontard, Candice Botuha, Michele Salmain

EUROPEAN JOURNAL OF INORGANIC CHEMISTRY (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

A Solvent-free, Catalyst-free Formal [3+3] Cycloaddition Dearomatization Strategy: Towards New Fluorophores for Biomolecules Labelling

Liang Chang, Nathalie Fischer-Durand, Geoffrey Gontard, Benoit Bertrand, Serge Thorimbert, Luc Dechoux

Summary: A novel dearomatization reaction for nitrogen-containing heterocycles was developed, utilizing biorenewable methyl coumalate as an efficient partner under solvent-free conditions. This reaction successfully converted nine types of basic aromatic rings into their pyrido[1,2-a] fused derivatives, with good to excellent yields. The fluorescence properties of the products were harnessed for conjugating fluorescent tags to bovine serum albumin (BSA) and immunoglobulin G.

CHEMSUSCHEM (2021)

添加到收藏夹

Article Chemistry, Medicinal

Cytotoxic BODIPY-Appended Half-Sandwich Iridium(III) Complex Forms Protein Adducts and Induces ER Stress

Robin Ramos, Jean-Francois Gilles, Romain Morichon, Cedric Przybylski, Benoit Caron, Candice Botuha, Anthi Karaiskou, Michele Salmain, Joelle Sobczak-Thepot

Summary: IrBDP, a half-sandwich complex of iridium(III), containing a fluorescent and lipophilic BODIPY reporter group, is being developed as a potential anticancer drug candidate. Studies show that IrBDP quickly permeates the plasma membrane and accumulates in the mitochondria and endoplasmic reticulum, leading to cellular response and potential cytotoxicity.

JOURNAL OF MEDICINAL CHEMISTRY (2021)

添加到收藏夹

Article Chemistry, Organic

Iron Catalyzed Dearomatization of Pyridines into Annelated Azepine Derivatives in a One-Step, Three-Component Reaction

Alexander Mamontov, Liang Chang, Heloise Dossmann, Benoit Bertrand, Luc Dechoux, Serge Thorimbert

Summary: In this study, commercially available Fe(TTP)Cl catalyst was used to catalyze the three-component dearomative formal cycloaddition reactions between pyridines, diazo compounds, and coumalates at room temperature. Diversely substituted annelated seven-membered N-heterocycles could be synthesized in less than 10 minutes with high efficiency. The study also demonstrated the successful substitution of benzimidazoles for pyridines in this reaction.

ORGANIC LETTERS (2022)

添加到收藏夹

Article Materials Science, Multidisciplinary

3-Hydroxypyridinyl-Substituted-1,2,4-Triazoles as New ESIPT Based Fluorescent Dyes: Synthesis and Structure-Fluorescence Properties Correlations

Anthony Nina-Diogo, Benoit Bertrand, Serge Thorimbert, Geoffrey Gontard, Sehr Nassem-Kahn, Andrea Echeverri, Julia Contreras-Garcia, Clemence Allain, Gilles Lemercier, Eleonora Luppi, Candice Botuha

Summary: This report presents the design, synthesis, and photophysical study of two new series of promising fluorescent trisubstituted triazoles, PyOHTr and PyCOTr. The PyOHTr molecules were found to exhibit an excited state intramolecular proton transfer (ESIPT) fluorescence mechanism through ab initio theoretical calculations. These fluorescent dyes possess unique optical properties with potential applications in medicinal chemistry and materials science.

ADVANCED OPTICAL MATERIALS (2023)

添加到收藏夹

Article Chemistry, Organic

1,6-Naphthyridin-7(6H)-ones: synthesis and optical properties

Anissa Beghennou, Geoffrey Gontard, Heloise Dossmann, Kevin Passador, Serge Thorimbert, Vincent Corce, Candice Botuha

Summary: Efficient synthesis of original 1,6-naphthyridin-7(6H)-ones and their optical properties, including dual fluorescence, solvatochromism, acidochromism, large Stokes shifts, and high quantum yields, are described in this study. These properties make them suitable for biological applications or as luminescent devices in materials science.

ORGANIC & BIOMOLECULAR CHEMISTRY (2023)

添加到收藏夹

Article Chemistry, Physical

In silico design of bio-marker detection fluorescent probes

Andrea Echeverri, Candice Botuha, Tatiana Gomez, Eleonora Luppi, Julia Contreras-Garcia, Carlos Cardenas

Summary: Fluorescent probes that can sense the biological medium are extremely important in medical diagnostics. This paper showcases the in-silico design of potential fluorescent biomarkers that fulfill two important conditions - emission wavelength within the optical window of 650 to 950 nm and a large Stokes shift, greater than 150 nm.

PHYSICAL CHEMISTRY CHEMICAL PHYSICS (2023)

添加到收藏夹

Article Chemistry, Inorganic & Nuclear

Insights into the antiproliferative mechanism of (C∧N)-chelated half-sandwich iridium complexes

Robin Ramos, Jeremy M. Zimbron, Serge Thorimbert, Lise-Marie Chamoreau, Annie Munier, Candice Botuha, Anthi Karaiskou, Michele Salmain, Joelle Sobczak-Thepot

DALTON TRANSACTIONS (2020)

添加到收藏夹

暂无数据

© Peeref 2019-2024. All rights reserved.