Three Dihydroquinolin-4-one Derivatives as Potential Biodiesel Additives: From the Molecular Structure to Machine Learning Approach DOI Creative Commons
Leonardo R. Almeida, Antônio S. N. Aguiar,

Alex B. R. M. da Anunciação

и другие.

ACS Omega, Год журнала: 2024, Номер 9(50), С. 49188 - 49204

Опубликована: Дек. 9, 2024

Biodiesel offers an alternative to fossil fuels, primarily because it is derived from renewable sources, with the potential mitigate issues such as pollutant and greenhouse gas emissions, resource scarcity, market instability of petroleum derivatives. However, lower durability stability pose challenges. To address this, researchers worldwide are exploring technologies that employ specific molecules slow down biodiesel's oxidation process, thereby preserving its key physicochemical properties. This study investigates heterocyclic dihydroquinolinone derivatives additives enhance oxidative diesel-biodiesel blends. Comprehensive structural computational analyses were carried out by density functional theory investigate reactivity aspects these compounds additive candidates. The supramolecular arrangements predominantly stabilized weak molecular interactions, C-H···O C-H···π, which associated antioxidant antibacterial We demonstrate groups can act electron-donating or electron-withdrawing substituents. explored frontier orbitals, provide insights into chemical reactivity, acidity, basicity, best oxidizing reducing agents. Finally, maps indicate nucleophilic electrophilic regions Fukui indices show sites nucleophilic, electrophilic, radical attacks. comprehensive paves way understanding how dihydroquinolinone-based serve alternatives for fuel additives.

Язык: Английский

Copper-catalyzed dehydrogenative cyclization/alkenylation towards dihydroquinolinones DOI

K. Pari,

Nawaz Khan Fazlur-Rahman

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(20), С. 4163 - 4171

Опубликована: Янв. 1, 2024

A mild and one-pot sequential route to access diversely substituted quinolinyl dihydroquinolinones has been proposed, using a dehydrogenative cyclization/alkenylation strategy with good yields.

Язык: Английский

Процитировано

6

Natural 3,4-dihydro-2(1 H )-quinolinones- Part I: plant sources DOI

Shahriar Khadem,

Robin J. Marles

Natural Product Research, Год журнала: 2024, Номер unknown, С. 1 - 16

Опубликована: Май 8, 2024

While natural products have undoubtedly played a pivotal role in drug discovery, their potential as lead compounds has been hindered by challenges such limited accessibility and complex synthesis processes. At the core of numerous synthetic compounds, each exhibiting remarkable biological traits, lies foundational structure 3,4-dihydro-2(1

Язык: Английский

Процитировано

6

Recent developments for the synthesis of the dihydroisoquinolin-1(2H)-ones via cyclization of N-allylbenzamides DOI
Yan‐Ning Niu, Keyu Wang, Fuzhong Han

и другие.

Tetrahedron, Год журнала: 2025, Номер unknown, С. 134497 - 134497

Опубликована: Янв. 1, 2025

Язык: Английский

Процитировано

0

Natural 3,4-Dihydro-2(1 H )-quinolinones – part III: biological activities DOI

Shahriar Khadem,

Robin J. Marles

Natural Product Research, Год журнала: 2024, Номер unknown, С. 1 - 8

Опубликована: Май 25, 2024

Natural products have played a crucial role in drug discovery, but their development is hindered by challenges such as inadequate availability and complex synthesis methods. However, both natural synthetic compounds that the core structure of 3,4-dihydro-2(1

Язык: Английский

Процитировано

3

Asymmetric Synthesis of 3,4‐Dihydroquinolin‐2‐ones via Organocatalytic [4+2]‐Cyclization of 2‐Amino‐β‐nitrostyrenes with Azlactones DOI

Heebum Kim,

Yeongju Kim,

Sung‐Gon Kim

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(8), С. 1756 - 1762

Опубликована: Фев. 29, 2024

Abstract Dihydroquinolin‐2‐ones, recognized for their bioactive properties, feature a six‐membered structure with nitrogen‐containing heterocycles. A method has been developed synthesizing enantioenriched 3,4‐dihydroquinoline‐2‐one derivatives. This approach utilizes an asymmetric [4+2]‐cyclization process, combining 2‐amino‐β‐nitrostyrenes azlactones, and is facilitated by bifunctional squaramide‐based organocatalyst. process enabled the creation of chiral 3,4‐dihydroquinoline‐2‐ones complex structures, including tetrasubstituted carbon stereocenters, delivering corresponding products in 26–95% yield diastereomeric ratio 1.2:1–19:1 52–97 ee.

Язык: Английский

Процитировано

2

Regioselective tandem sulfonylation/cyclization of unsaturated N-substituted enamides with sulfonyl chlorides by copper catalysis DOI
Ran Ding, Tao Wu, Tao Ma

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(20), С. 5784 - 5790

Опубликована: Янв. 1, 2024

The radical cascade cyclization of vinyl-tethered alkenes has become a promising tool for rapidly assembling nonbenzene-fused cyclic skeletons via the cracking alkenyl C–H bonds, but this approach been limited to generate five-membered rings.

Язык: Английский

Процитировано

2

TMSOTf‐Promoted Synthesis of Quinazolin‐4(3H)‐one Utilizing DMSO as a Carbon Source DOI
Sumit Kumar,

R. Sivakumar,

Kishor Padala

и другие.

ChemistrySelect, Год журнала: 2023, Номер 8(42)

Опубликована: Ноя. 8, 2023

Abstract An efficient TMSOTf‐promoted multicomponent reaction has been developed for the one‐pot synthesis of quinazolin‐4 (3 H )‐ones. Using TMSOTf as a Lewis acid promoter and DMSO carbon source, isatoic anhydride, primary amines yielded variety quinazolines‐4 Additionally, promoted 2‐amino‐ N ‐substituted benzamide with yielding same scaffolds in high yields. However, use DMSO‐d 6 solvent enabled incorporation −CD moiety )‐one skeleton. This proves that plays twin role C1 source solvent. Various functional groups containing wide range )‐ones other heterocycles were employing this methodology. Also, synthetic methodology extended 3‐(2‐carboxyphenyl)‐4‐(3 )‐quinazolinone, an anti‐endotoxic drug.

Язык: Английский

Процитировано

5

Cu(ii)-catalyzed synthesis of N-sulfonated quinolin-2(1H)-one-3-carboxamides DOI
Xue Chen, Sheng Fang, Quan Zhou

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

Herein, we present an efficient Cu( ii )-catalyzed cascade synthesis of sulfonated 3-carboxamide quinolin-2-(1 H )-ones. Inthis paper, sulfonylhydrazides underwent unusual N–N bond cleavage and functioned as sulfamide synthons.

Язык: Английский

Процитировано

1

One-Pot Sequential Synthesis of Alkenylated Dihydroquinolinones and Hexahydroacridinones in Deep Eutectic Solvent Medium DOI Creative Commons

Sundararajan Suresh,

Fazlur‐Rahman Nawaz Khan

ACS Omega, Год журнала: 2024, Номер unknown

Опубликована: Авг. 16, 2024

The sequential synthesis of N-heterocycles from saturated ketones poses significant challenges and has rarely been reported. Herein, an efficient alkenylated dihydroquinolinones 7 hexahydroacridinones 8 is achieved 1 or 2 via dehydrogenation, cyclization, oxidation, α-alkenylation in choline chloride-based deep eutectic solvent (DES) medium. This strategy provides excellent yield low-cost, readily available starting materials under environmentally benign conditions. Furthermore, the synthesized compounds (4, 5, 7, 8) were investigated for their photophysical properties through absorption emission spectral studies.

Язык: Английский

Процитировано

0

Constructing spirooxindoles from non-oxindole precursors: a one-pot nitro-reduction/double lactamization approach to spiro[indoline-3,3'-quinoline]-2,2'-diones DOI

Raju Chouhan,

Abhijit Gogoi, Sajal Kumar Das

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(37), С. 7601 - 7606

Опубликована: Янв. 1, 2024

2-(2-Nitrobenzyl)-2-(2-nitrophenyl)malonates, readily prepared by S

Язык: Английский

Процитировано

0