N-Carboxyanhydrides Directly from Amino Acids and Carbon Dioxide and their Tandem Reactions to Therapeutic Alkaloids DOI Creative Commons
Thi V. Tran, Yi Shen, Hieu D. Nguyen

et al.

Published: Oct. 12, 2022

We report on the preparation of synthetically versatile N-carboxyanhydrides (NCAs) directly from amino acids and CO2 using n-propylphosphonic anhydride. Most NCAs were isolated with >95% purity after simple workup, avoiding need for tedious purification procedures typically required conventional methods. Because reagents conditions employed are mild, tandem reactions moisture-sensitive carried out to transform them into medicinally active alkaloids tryptanthrin phaitanthrin A in one pot. qualitative analysis revealed that our NCA synthesis approach is more green than methods, which all or indirectly use highly poisonous gas phosgene.

Language: Английский

Arylcarboxylation of unactivated alkenes with CO2 via visible-light photoredox catalysis DOI Creative Commons
Wei Zhang, Zhen Chen, Yuan‐Xu Jiang

et al.

Nature Communications, Journal Year: 2023, Volume and Issue: 14(1)

Published: June 14, 2023

Photocatalytic carboxylation of alkenes with CO2 is a promising and sustainable strategy to synthesize high value-added carboxylic acids. However, it challenging rarely investigated for unactivated due their low reactivities. Herein, we report visible-light photoredox-catalyzed arylcarboxylation CO2, delivering variety tetrahydronaphthalen-1-ylacetic acids, indan-1-ylacetic indolin-3-ylacetic chroman-4-ylacetic acids thiochroman-4-ylacetic in moderate-to-good yields. This reaction features chemo- regio-selectivities, mild conditions (1 atm, room temperature), broad substrate scope, good functional group compatibility, easy scalability facile derivatization products. Mechanistic studies indicate that situ generation carbon dioxide radical anion following addition might be involved the process.

Language: Английский

Citations

53
Recent advances of tryptanthrin and its derivatives as potential anticancer agents DOI
Xiaofeng Zhou

RSC Medicinal Chemistry, Journal Year: 2024, Volume and Issue: 15(4), P. 1127 - 1147

Published: Jan. 1, 2024

Tryptanthrin with a broad spectrum of biological activities can be not only decorated by various functional groups, but also coordinated bio-metal ions, generating varied tryptanthrin derivatives as potential anticancer agents low toxicity.

Language: Английский

Citations

11
Unlocking the photo-dehydrogenation ability of naphthalene monoimide towards the synthesis of quinazolinones DOI

Supriya Halder,

Sourav Mandal, Ayanangshu Biswas

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(7), P. 2840 - 2845

Published: Jan. 1, 2023

A photocatalytic method involving naphthalene monoimide has been shown to synthesize quinazolinones under very mild reaction conditions.

Language: Английский

Citations

16
Titanocene dichloride-catalyzed synthesis of heterocycles accelerated by in-situ formed Lewis and Brønsted acids DOI
Yuanyong Yao,

Li Tu,

Xiu Wang

et al.

Molecular Catalysis, Journal Year: 2025, Volume and Issue: 573, P. 114822 - 114822

Published: Jan. 18, 2025

Language: Английский

Citations

0
Symmetrical Bis-Hydrazone Ligand-Based Binuclear Oxido/Dioxido-Vanadium(IV/V) Complexes: Synthesis, Reactivity, and Catalytic Applications for the Synthesis of Biologically Potent 2-Phenylquinazolin-4-(3H)-ones DOI
Mannar R. Maurya,

Monojit Nandi,

Sonu Kumar

et al.

Inorganic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 22, 2025

Symmetrical bis(hydrazone)-based ligands, H4dar(bhz)2 (I), H4dar(fah)2 (II), H4dar(nah)2 (III), and H4dar(inh)2 (IV) obtained from 4,6-diacetylresorcinol (H2dar) different hydrazides [benzoylhydrazide (Hbhz), isonicotinoylhydrazide (Hinh), nicotinoylhydrazide (Hnah), 2-furoylhydrazide (Hfah)], were used to prepare potassium salts of binuclear cis-[VVO2]+ complexes, {K(H2O)2}2[(VVO2)2dar(bhz)2] (1), {K(H2O)2}2[(VVO2)2dar(fah)2] (2), {K(H2O)2}2[(VVO2)2dar(nah)2] (3), {K(H2O)2}2[(VVO2)2dar(inh)2] (4), [VIVO]2+ [{VIVO(MeOH)}2dar(bhz)2] (5), [{VIVO(MeOH)}2dar(fah)2] (6), [{VIVO(MeOH)}2dar(nah)2] (7), [{VIVO(MeOH)}2dar(inh)2] (8). In the presence warm MeOH/DMSO (4:1), 3 changed {K(H2O)2}[(VVO2)2Hdar(nah)2]·DMSO (3a·DMSO). Single crystal XRD studies 1 3a confirm a structure along with distorted square pyramidal geometry each vanadium center where bis{ONO(2-)} ligands coordinate through phenolate-O, azomethine-N, enolate-O atoms unit. While growing crystals 6 in EtOH, part it oxidizes gives [{VVO(OEt)}2dar(fah)2] (9) powdery 6. Complex 9 has octahedral structure. These complexes as catalysts for synthesis biologically important 2-phenylquinazolin-4-(3H)-ones having aryl aldehydes, they all show excellent catalytic performance (up 97% yield) less reaction time low temperature, 70% aqueous TBHP/30% H2O2 greener oxidant. Generally, these perform better than their mononuclear analogues. Spectroscopy, DFT studies, isolated intermediates have helped proposing suitable mechanism reaction.

Language: Английский

Citations

0
<i>ortho</i>-Functionalized nitroarenes in the synthesis of heterocycles DOI
Vera L. Mamedova,

Sevil V. Mamedova,

Dmitry E. Korshin

et al.

Russian Chemical Reviews, Journal Year: 2025, Volume and Issue: 94(4), P. RCR5167 - RCR5167

Published: April 1, 2025

The development of convenient methods for the synthesis heterocyclic compounds that are highly important search pharmacological substances and in other spheres human activity is among most relevant fields organic chemistry. Two functional groups arenes located adjacent positions benzene ring can provide a fused ring. If at least one two <i>ortho</i>-functional contains nitrogen atom, heterocycle formed upon cyclization. nitro group often chosen as nitrogen-containing <i>ortho</i>-substituted to form systems, because ready availability <i>ortho</i>-functionalized nitroarenes, ability undergo various reactions selectivity reactions. This review integrates analyzes first time published data on involvement nitroarenes design structures. Using numerous examples reported literature last decade, mutually beneficial effect groups, which group, formation heterocycles demonstrated. Examples both intramolecular cyclizations involving additional reagents considered. gives holistic view potential functionalized <i>ortho</i>-nitroarenes systems. <br> bibliography includes 132 references.

Language: Английский

Citations

0
Direct Photocatalytic Reductive Amidation of Nitroarenes: A Tandem Reduction–Decarboxylation Approach to Amide Bond Construction DOI
Chenwei Liu, Xiaowen Qin,

Weiheng Yuan

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: May 15, 2025

We report a photocatalytic strategy for direct amide synthesis from readily available nitroarenes and benzoylformic acids using flavin as an efficient photocatalyst. This one-pot transformation proceeds through tandem reduction-decarboxylation-amidation sequence under mild blue light irradiation. Preliminary mechanistic studies indicated that nitrosoarene N-hydroxyamides could be the key intermediates. The method demonstrates broad substrate scope, excellent functional group tolerance, remarkable operational simplicity, it can conducted ambient atmosphere. Notably, this protocol represents significant advancement in step economy by directly employing diverse nitrogen sources, avoiding need pre-reduced amine

Language: Английский

Citations

0
An Aldehyde-Driven, Fe(0)-Mediated, One-Pot Reductive Cyclization: Direct Access to 5,6-Dihydro-quinazolino[4,3-b]quinazolin-8-ones and Photophysical Study DOI
Subrata Sahoo,

Manthri Atchuta Rao,

Shantanu Pal

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(15), P. 10701 - 10710

Published: July 20, 2023

A short, proficient, and regioselective synthesis of biheterocyclic 5,6-dihydro-quinazolino[4,3-b]quinazolin-8-ones has been revealed via an Fe(0)-powder-mediated, one-pot reductive cyclization protocol. Mechanistic investigation proved that water acts as a source hydrogen for the reduction nitro group reaction rate was accelerated by aldehyde. The designed transformation works under aerobic conditions, providing series bio-inspired molecular scaffolds. In addition, photophysical study showed blue fluorescence emission with good quantum yield.

Language: Английский

Citations

7
Cobalt-Centered Supramolecular Nanoensemble for Regulated Aerobic Oxidation of Alcohols and “One-Pot” Synthesis of Quinazolin-4(3H)-ones DOI
S. Lokesh Kumar, M. Kumar, Vandana Bhalla

et al.

ACS Applied Materials & Interfaces, Journal Year: 2023, Volume and Issue: 15(42), P. 49246 - 49258

Published: Oct. 16, 2023

The supramolecular assemblies of the donor–acceptor (D–A) system Im-Tpy, having phenanthro[9,10-d]imidazole as donor and terpyridyl group acceptor unit, have been developed, which serve host to stabilize Co(II) in its nanoform. as-prepared nanoensemble Im-Tpy@Co DMSO:water (7:3) shows high thermal stability photostability. Even case solvent mismatch, i.e., on dilution with cosolvent THF/DMSO, insignificant changes were observed size/morphology nanoensemble. low catalytic loading (0.1 mol % Co) catalyzes oxidation a wide variety alcohols aromatic aldehydes/ketones using visible light radiations source energy without need any additive at room temperature. In comparison already reported systems, exhibits turnover numbers (TONs) frequencies (TOFs). practical application has also demonstrated gram-scale synthesis 4-chlorobenzaldehyde. recyclability up four cycles leaching morphological changes. present study demonstrates activity "one-pot" quinazolin-4(3H)-ones from 2-aminobenzamide primary better efficiency other transition-metal-based systems.

Language: Английский

Citations

7
N-Carboxyanhydrides directly from amino acids and carbon dioxide and their tandem reactions to therapeutic alkaloids DOI
Thi V. Tran, Yi Shen, Hieu D. Nguyen

et al.

Green Chemistry, Journal Year: 2022, Volume and Issue: 24(23), P. 9245 - 9252

Published: Jan. 1, 2022

A phosgene-free method to prepare N -carboxyanhydrides from amino acids and carbon dioxide has been developed. This is mild enough be used in the tandem synthesis of alkaloids tryptanthrin phaitanthrin A.

Language: Английский

Citations

11