Article
Biochemistry & Molecular Biology
Jianwei Shi, Zhichuan Wang, Xiaoxu Teng, Bing Zhang, Kai Sun, Xin Wang
Summary: In this study, we achieved a C3-selenylation of pyrido[1,2-a]pyrimidin-4-ones using an electrochemically driven external oxidant-free strategy. Various structurally diverse seleno-substituted N-heterocycles were obtained in moderate to excellent yields. A plausible mechanism for this selenylation was proposed based on radical trapping experiments, GC-MS analysis, and cyclic voltammetry study.
Article
Chemistry, Organic
Rajesh T. T. Bhawale, Umesh A. A. Kshirsagar
Summary: A metal-catalyst-free, organic dye-catalyzed C3-H arylation of pyrido[1,2-a]pyrimidin-4-ones using visible light irradiation was developed. This simple and direct C-H functionalization approach effectively produced biologically significant C3 arylated pyrido[1,2-a]pyrimidin-4-one and thiazolo[3,2-a]pyrimidin-5-one derivatives, including medicinally important endothelial cell dysfunction inhibitor and anti-inflammatory agents with good functional group tolerance. The photoinduced direct C3-H arylation approach is suitable for scale-up synthesis.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Baichuan Mo, Chunxia Chen, Jinsong Peng
Summary: Various multi-substituted pyrido[1,2-a]pyrimidin-4-ones were synthesized through a one-pot tandem CuI-catalyzed C-N bond formation/intramolecular amidation reaction at 130 °C in DMF. This protocol allows for practical and modular synthesis of pyrido[1,2-a]pyrimidin-4-ones from readily available 2-halopyridine and (Z)-3-amino-3-arylacrylate ester in good to excellent yields, with simple operation, broad substrate scope, good functional group tolerance, and gram scale preparation.
Article
Chemistry, Organic
Lina Guo, Meiyun Su, Haiying Zhan, Wenjie Liu, Shaohua Wang
Summary: An efficient and simple protocol for silver-catalyzed direct C3 phosphonation of 4H-pyrido[1,2-a]pyrimidin-4-ones with dialkyl phosphites has been developed, showing high regioselectivity, broad scope of substrates, and good functional group compatibility. Importantly, the phosphorylated product can be used as efficient probes for Fe3+.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Sumeyye Yalduz, Mehmet Yilmaz
Summary: In this study, furo[2,3-d]pyrido[1,2-a]pyrimidin-4-ones were synthesized by microwave-assisted radical cyclizations. The reaction was performed between 2-hydroxy-4H-pirido[1,2-a]pirimidin-4-ones and conjugated alkenes and phenylacetylene using Mn(OAc)(3) as a catalyst. Different reaction conditions were compared to optimize the reaction. The obtained compounds were characterized using spectroscopic techniques and XRD analysis.
Article
Chemistry, Multidisciplinary
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.
Article
Chemistry, Applied
Prasanjit Ghosh, Gautam Chhetri, Eliyahu Perl, Sajal Das
Summary: The methodology reported involves the arylselenylation of 4H-Pyrido-[1,2-a]-Pyrimidin-4-ones using readily available organodiselenides in high yields up to 98%, without the need for a metal catalyst. Additionally, it can be applied for the synthesis of ArSe substituted 5H-thiazolo-pyrido[3,2-a]pyrimidin-4-ones.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
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)
Article
Chemistry, Multidisciplinary
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.
Article
Chemistry, Organic
Qian Gao, Jia-Ming Lu, Lingyun Yao, Siqi Wang, Jun Ying, Xiao-Feng Wu
Summary: A cobalt-catalyzed direct CH carbonylative reaction of N-(2-(1H-indol-1-yl)phenyl)picolinamides for the synthesis of (NH)-indolo[1,2-a]quinoxalin-6(5H)-one skeletons has been developed. Various free (NH)-indolo[1,2-a]quinoxalin-6(5H)-ones were obtained in good yields (up to 88%) using benzene-1,3,5-triyl triformate (TFBen) as the CO source and picolinamide as the traceless directing group. Additionally, a series of product derivatizations were demonstrated, and the core fragment of PARP-1 inhibitor C can be readily constructed by this protocol.
Article
Chemistry, Organic
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)
Article
Chemistry, Multidisciplinary
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)
Article
Chemistry, Organic
Lina Guo, Meiyun Su, Junliang Lv, Wenjie Liu, Shaohua Wang
Summary: A novel and efficient method for regioselective selenylation of 4H-pyrido-[1,2-a]-pyrimidin-4-ones with diselenides at room temperature has been developed. The procedure is catalyzed by N-iodosuccinimide under metal-free conditions and provides good to excellent yields of C3 selenylation products across a broad range of substrates. Furthermore, sulfenylation with diphenyl disulfides and 4-methylbenzenethiol in this transformation is also successful.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Le-Cheng Wang, Yu Zhang, Zhengkai Chen, Xiao-Feng Wu
Summary: A procedure for the palladium-catalyzed carbonylative reaction has been developed for the synthesis of pharmaceutically valuable 2-(trifluoromethyl)quinazolin-4(3H)-ones. The transformation uses Mo(CO)(6) as both a convenient CO source and a reducing reagent. This newly developed protocol is compatible with various nitro compounds and can be readily scaled up to a 1 mmol scale.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Sai Deepak Pasuparthy, Barnali Maiti
Summary: A novel synthetic route for the synthesis of chromeno[4,3-d]pyrido[1,2-a]pyrimidin-6-one derivatives was developed using an acid ionic liquid via one-pot, three-component synthesis. The synthesized derivatives were well characterized and their photophysical properties were determined.
Review
Chemistry, Multidisciplinary
Dan He, Yawen Li, Fuwen Zhao, Yuze Lin
Summary: High trap density in organic solar cells leads to localized charge carriers and reduced carrier lifetime, limiting device efficiency. This feature article summarizes the recent advances of trap suppression by material design and device engineering.
CHEMICAL COMMUNICATIONS
(2024)
Review
Chemistry, Multidisciplinary
Olivier Monfort, Arshitha Madhusudhan, Martin Motola
Summary: This article presents the advantages of coupling photocatalysis and Fenton-based processes for environmental remediation and discusses their synergy. It critically examines the simultaneous triggering of these two processes and provides insights into research approaches. The study aims to enhance understanding of this complex process and highlight the potential integration of new catalysts in current wastewater treatment technology.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Manideepa Dhar, Chittaranjan Mishra, Avijit Das, Uttam Manna
Summary: An approach of 'polymerization of monomers in its aggregated form' has been introduced to tailor the water wettability of fibrous and porous substrates, achieving hydrophobicity to superhydrophobicity transition, as well as patterned wettability. This facile chemical method provides a durable coating with adjustable and patterned wettability for various potential applications.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Saswat Ranjan Bhoi, Chhanda Debnath, Shikha Gandhi
Summary: In this article, a novel catalytic reaction using Pd(0) and Bronsted acid is reported for the synthesis of biologically important imidazolidinone-fused N-heterocycles through redox-neutral intramolecular N-allylation of indoles and pyrroles with alkynes. This atom-economical method is applicable to a wide range of substrates and eliminates the need for leaving groups or oxidizing agents commonly used in traditional allylation reactions.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Longkun Chen, Mingshuai Zhang, Meichen Liu, Zhuoyuan Liu, Yuetong Qiu, Zhilai Zhang, Fuchao Yu, Jiuzhong Huang
Summary: In this study, an efficient Rh(III)-catalyzed selective mono- and dual-C-H bond functionalization/cyclization with iodonium ylide as the sole coupling partner was demonstrated. Fused benzodiazepine skeletons were obtained in excellent yields, providing an improved approach to dual C-H unsymmetrical functionalization.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Alice Kennett, Sven Epple, Gabriella van der Valk, Irene Georgiou, Evelyne Gout, Romain R. Vives, Angela J. Russell
Summary: This study presents the design and synthesis of sulfated disaccharide inhibitors based on IdoA(2S)-GlcNS(6S), which showed potent inhibition of Sulf-2. The results suggest that IdoA(2S)-GlcNS(6S) is the shortest fragment size required for effective inhibition of Sulfs, and a trisulfated disaccharide is identified as the minimal fragment size of heparan sulfate for effective endosulfatase inhibition.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Mauro Garbini, Andrea Brunetti, Riccardo Pedrazzani, Magda Monari, Massimo Marcaccio, Giulio Bertuzzi, Marco Bandini
Summary: The self-adaptability of galvanostatic electrolysis was found to be helpful in a multistage chemo- and diastereoselective electrochemically promoted cyclodimerization of chalcones. Through a series of reductive events, densely functionalized cyclopentanes with five contiguous stereocenters were obtained (25 examples, yields up to 95%, dr values up to >20:1). Further experimental and electrochemical investigations indicated the crucial role of dynamic kinetic resolution of the aldol intermediate in the reaction mechanism.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Dhananjay S. Nipate, Neha Meena, Prakash N. Swami, Krishnan Rangan, Anil Kumar
Summary: In this study, the synthesis of functionalized benzo[a]phenazines and indazolo[2,3-a]quinolines was achieved through Rh(III)-catalyzed oxidative annulation of 2-arylquinoxalines and 2-aryl-2H-indazoles with allyl alcohols. The method showed a wide substrate scope, excellent functional group tolerance, good to high yields of annulated products, and the capability for scaled-up synthesis. A tentative mechanism of the annulation reaction was proposed based on a preliminary mechanistic investigation.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Ruonan Zhang, Abudukadi Tudi, Xia Yang, Xuping Wang, Zhihua Yang, Shujuan Han, Shilie Pan
Summary: A new lead tellurium borate material with a unique fundamental building block [B4O10] was synthesized and found to exhibit high birefringence. The structure-property relationship was discussed using first-principles calculations.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Amresh Kumar Singh, Baishali Thakurta, Anupam Giri, Monalisa Pal
Summary: This study introduces three key concepts for the quick synthesis of large-scale high-quality 2D materials films and their utilization in device fabrication.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Reina Hagiwara, Shun Nishimura, Kosuke Okeyoshi
Summary: A copolymer-conjugated nanocatalytic system has been developed to improve electron transfer and enhance photoinduced H2 generation.
CHEMICAL COMMUNICATIONS
(2024)