Iron-catalyzed one-pot synthesis of quinoxalines: transfer hydrogenative condensation of 2-nitroanilines with vicinal diols

Putta, Ramachandra Reddy; Chun, Sang-Hyun; Lee, Seok Beom; Hong, Junhwa; Oh, Dong Kyu; Hong, Suckchang

doi:10.1039/d1ra02532e

Cited by 12 publications

(75 citation statements)

References 53 publications

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“…13, 150.37, 139.42, 137.72, 135.20, 134.21, 130.75, 128.57, 128.24, 127.59, 127.11, 125.55, 122.91, 20.61, 16.81. 27 Yellow solid; mp 73-74 °C; yield: 210.7 mg (90%).…”

Section: -Propylquinazoline (3ap) 8bmentioning

confidence: 99%

“…30, 160.43, 150.83, 139.64, 136.90, 135.66, 134.05, 130.08, 129.60, 128.54, 127.15, 127.00, 126.17, 123.51, 19.95, 19.90. 27 Yellow solid; mp 93-94 °C; yield: 215.4 mg (92%).…”

Section: -(34-dimethylphenyl)quinazoline (3ar)mentioning

confidence: 99%

“…13 C NMR (101 MHz, CDCl 3 ):  = 163. 46, 160.46, 150.56, 136.37, 134.36, 134.24, 131.29, 130.47, 129.75, 128.64, 128.57, 127.76, 127.18, 126.95, 125.98, 125.38, 123.13. 8-Methyl-2-(m-tolyl)quinazoline (3bc) 27 Yellow solid; mp 57-58 °C; yield: 210.7 mg (90%).…”

Section: -(Naphthalen-1-yl)quinazoline (3at) 8amentioning

confidence: 99%

“…13 C NMR (101 MHz, CDCl 3 ):  = 160. 46, 160.02, 149.67, 138.35, 138.16, 137.06, 133.80, 131.31, 129.12, 128.55, 126.82, 125.80, 124.79, 123.45, 21.67, 17. 27 Yellow solid; mp 127-128 °C; yield: 225.8 mg (91%).…”

Section: -(Naphthalen-1-yl)quinazoline (3at) 8amentioning

confidence: 99%

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Iridium-Catalyzed Acceptorless Dehydrogenative Coupling of 2-Aminoarylmethanols with Amides or Nitriles to Synthesize Quinazolines

Shui¹,

Zhong²,

Ouyang³

et al. 2022

Synthesis

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An efficient iridium-catalyzed acceptorless dehydrogenative coupling (ADC) reaction for the preparation of various quinazolines from 2-aminoarylmethanols and amides or nitriles had been developed. A wide range of substituted 2-aminobenzyl alcohols and (hetero)aryl or alkyl benzamides and nitriles were well compatible to afford various quinazolines in excellent yields. This new strategy merits the high atom-economy, mild reaction condition, simple operation and suited to a variety of substrates.

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“…13, 150.37, 139.42, 137.72, 135.20, 134.21, 130.75, 128.57, 128.24, 127.59, 127.11, 125.55, 122.91, 20.61, 16.81. 27 Yellow solid; mp 73-74 °C; yield: 210.7 mg (90%).…”

Section: -Propylquinazoline (3ap) 8bmentioning

confidence: 99%

“…30, 160.43, 150.83, 139.64, 136.90, 135.66, 134.05, 130.08, 129.60, 128.54, 127.15, 127.00, 126.17, 123.51, 19.95, 19.90. 27 Yellow solid; mp 93-94 °C; yield: 215.4 mg (92%).…”

Section: -(34-dimethylphenyl)quinazoline (3ar)mentioning

confidence: 99%

Section: -(Naphthalen-1-yl)quinazoline (3at) 8amentioning

confidence: 99%

Section: -(Naphthalen-1-yl)quinazoline (3at) 8amentioning

confidence: 99%

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Iridium-Catalyzed Acceptorless Dehydrogenative Coupling of 2-Aminoarylmethanols with Amides or Nitriles to Synthesize Quinazolines

Shui¹,

Zhong²,

Ouyang³

et al. 2022

Synthesis

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“…Consequently, several procedures of synthesizing benzopyrazines have been reported in the literature. A few synthetic procedures, reported in the immediate past, include the synthesis of benzopyrazines under the catalytic influence of Co 3 O 4 nanocages based nickel catalyst (Sharma et al, 2021), iron-catalyzed transfer hydrogenative condensation (Putta et al, 2021), sodium hydroxide-mediated hydrogen-transfer (Wang et al, 2021), as well as the uses of tungstophosphoric acid-support (Kumaresan et al, 2020), and Co-based nanocatalyst (Panja et al, 2020).…”

Section: Introductionmentioning

confidence: 99%

Benzopyrazine-Based Small Molecule Inhibitors As Trypanocidal and Leishmanicidal Agents: Green Synthesis, In Vitro, and In Silico Evaluations

et al. 2021

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World Health Organization (WHO) identified twenty tropical disease categories as neglected tropical diseases (NTDs)1. Chagas’ disease (also known as American trypanosomiasis) and leishmaniasis are two major classes of NTDs. The total number of mortality, morbidity, and disability attributed each year due to these two categories of diseases in magnitudes is much higher than the so-called elite diseases like cancer, diabetes, AIDS, cardiovascular and neurodegenerative diseases. Impoverished communities around the world are the major victim of NTDs. The development of new and novel drugs in the battle against Chagas’ disease and leishmaniasis is highly anticipated. An easy and straightforward on-water green access to synthesize benzopyrazines is reported. This ultrasound-assisted procedure does not require any catalyst/support/additive/hazardous solvents and maintains a high atom economy. A series of eleven benzopyrazines has been synthesized, and most of the synthesized compounds possess the drug-likeness following Lipinski’s “Rule of 5”. Benzopyrazines 3 and 4 demonstrated moderate leishmanicidal activity against L. mexicana (M378) strain. The selective lead compound 1 showed good leishmanicidal, and trypanocidal activities (in vitro) against both L. mexicana (M378) and T. cruzi (NINOA) strains compared to the standard controls. The in vitro trypanocidal and leishmanicidal activities of the lead compound 1 have been validated by molecular docking studies against four biomolecular drug targets viz. T. cruzi histidyl-tRNA synthetase, T. cruzi trans-sialidase, leishmanial rRNA A-site, and leishmania major N-myristoyl transferase.

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Recent Developments in Manganese, Iron and Cobalt Homogeneous Catalyzed Synthesis of Primary Amines via Reduction of Nitroarenes, Nitriles and Carboxamides

Darcel

2023

Adv Synth Catal

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The preparation of primary amines attracts huge attention in the molecular synthetic community. Indeed, amines play a crucial role in chemistry as they are important substructures in a huge amount of drug molecules, agrochemicals, dyes and molecular materials. Compared to stoichiometric reductions using metal hydride based reagents, the catalyzed reduction of nitroarenes, nitriles and carboxamides appears to be an attractive option, mainly when associated to first row transition metals such as manganese, iron, or cobalt. In this short review, we illustrate the progress achieved in homogeneous hydrogenation, hydrogen transfer, hydrogen borrowing and hydrosilylation of nitroarenes, nitriles and carboxamides.

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Iron-catalyzed one-pot synthesis of quinoxalines: transfer hydrogenative condensation of 2-nitroanilines with vicinal diols

Abstract: A transfer hydrogenative condensation between 2-nitroanilines and vicinal diols for the synthesis of quinoxalines, with no additional oxidant, reductant and base.

Cited by 12 publications

References 53 publications

Iridium-Catalyzed Acceptorless Dehydrogenative Coupling of 2-Aminoarylmethanols with Amides or Nitriles to Synthesize Quinazolines

Iridium-Catalyzed Acceptorless Dehydrogenative Coupling of 2-Aminoarylmethanols with Amides or Nitriles to Synthesize Quinazolines

Benzopyrazine-Based Small Molecule Inhibitors As Trypanocidal and Leishmanicidal Agents: Green Synthesis, In Vitro, and In Silico Evaluations

Recent Developments in Manganese, Iron and Cobalt Homogeneous Catalyzed Synthesis of Primary Amines via Reduction of Nitroarenes, Nitriles and Carboxamides

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