Microwave-assisted one-pot synthesis of 2,3-disubstituted 3H-quinazolin-4-ones

doi:10.1016/j.tetlet.2005.01.008

Tetrahedron Letters

Volume 46, Issue 8, 21 February 2005, Pages 1241-1244

https://doi.org/10.1016/j.tetlet.2005.01.008 Get rights and content

Abstract

A practical synthesis of 2,3-disubstituted 3H-quinazolin-4-ones 1 with broad chemistry scope is described. The key step is the microwave promoted one-pot, two-step reaction sequence combining anthranilic acids, carboxylic acids, and amines providing efficient access to this important class of heterocycles.

Graphical abstract

Section snippets

Acknowledgements

The authors thank Dr. Daniel Yohannes for helpful discussion. The authors also thank Ms. Jun Zhao and Ms. Martina DeSomma for technical assistance.

References and notes (10)

T.G. Jackson et al.
J. Chem. Soc. (C)
(1968)
L.A. Errede
J. Org. Chem.
(1976)
G. Rabilloud et al.
J. Heterocyclic Chem.
(1980)
M. Okabe et al.
Tetrahedron
(1995)
B.L. Chenard et al.
J. Med. Chem.
(2001)
S. Xue et al.
J. Org. Chem.
(2004)
J.F. Wolfe et al.
J. Med. Chem.
(1990)
I.K. Kacker et al.
J. Indian Chem. Soc.
(1951)
A. Buzas et al.
Bull. Soc. Chim. Fr.
(1959)
W.M. Welch et al.
Bioorg. Med. Chem. Lett.
(2001)
(b)Ref....

There are more references available in the full text version of this article.

Cited by (151)

Catalyst- and solvent-free coupling of 2-methyl quinazolinones and 3-(trifluoroacetyl)coumarins: An environmentally benign access of quinazolinone derivatives
2023, Journal of Saudi Chemical Society
An environmentally benign highly atom-economic protocol for the construction of the CC bond has been developed under catalyst- and solvent-free conditions. This protocol involves the efficient coupling of 2-methyl quinazolinones with 3-(trifluoroacetyl)coumarins for the access of quinazolinone derivatives in excellent yields (up to 90 %). The crystal structure of compound 3di was investigated by X-ray diffraction analysis. The biological activities, such as in vitro antifungal activity of the quinazolinone derivatives against Fusarium graminearum, Fusarium moniliforme, Fusarium oxysporum, Phytophthora parasitica var nicotianae, and Rhizoctonia solani Kuhn, were investigated. The bioassay results indicated that most of the target products exhibited promising fungicidal activities, and compound 3 cl exhibited 95 % fungicidal activity against R. solani, with an EC₅₀ value of 10.6 μg/mL.
Synthesis of Quinazolin-4(3H)-ones via a novel approach
2023, Journal of Saudi Chemical Society
The present work was designed based on the new multi-component reaction, which forms 2-aryl/alkyl-quinazolin-4(3H)-ones in a one-pot reaction with good to excellent yields (86–97 %) using 2-aminobenzoic acid, organic acid, and ammonium hexafluorophosphate (NH₄PF₆). The advantages of the presented method include inexpensive and readily available starting materials, simple procedures, and easy workup. In this newly discovered method, ammonium hexafluorophosphate (NH₄PF₆) was used as a highly efficient reagent and catalyst for quinazolin-4(3H)-ones synthesis. All of the synthesized compounds were characterized by ¹H NMR and ¹³C NMR techniques.
Iron (II)-catalyzed diastereoselective cross-dehydrogenetive coupling of 2-methyl quinazolinones with indolin-2-ones
2021, Tetrahedron Letters
An efficient and highly diastereoselective synthesis of schizocommunin analogues has been achieved through an iron-catalyzed C(sp³)-H/C(sp³)-H cross-dehydrogenative coupling reaction between 2-methyl quinazolinones and indolin-2-ones. This method requires air (molecular oxygen) as an oxidant instead of chemical equivalent oxidising agents and prefunctionalized coupling partners. The developed schizocommunin analogues were obtained in good to excellent yields and various kinds of functional groups were tolerated. It is worthy to note that schizocommunin, a bioactive natural product displaying broad spectrum of biological properties in which anticancer property is one of them.
Microwave-Assisted Synthesis as an Efficient Method to Enhance the Catalytic Activity of Zr-Based Metal Organic Framework UiO-66 in a Heterocyclization Reaction
2019, Asian Journal of Organic Chemistry
Zr‐based metal‐organic frameworks have been considered promising heterogeneous catalysts in various reactions. It has been proven that the defect sites in these frameworks, which result from deficiency of linkers, could act as the reaction active sites. In this work, microwave irradiation was used for rapid synthesis and increasing defects on Zr₆ clusters of metal‐organic framework UiO‐66. Powder X‐ray diffraction, thermal gravimetric analysis, and N₂ sorption isotherms were performed to characterize and calculate the defect number in the framework. UiO‐66 prepared by microwave method for a few minutes could reach 1.8 missing linkers per cluster. The material with acetic acid as a co‐catalyst showed highly heterogeneous catalytic activity in the solvent‐free heterocyclization of 2,2‐disubstituted 2,3‐dihydroquinazolin‐4(1H)‐ones from anthranilamide and ketones/aldehydes. The synthetic scheme consisted of zirconium cluster catalysed carbonyl group of anthranilamide to achieve the C−N propitious combination and succeeding ring closure process.
One-Pot Synthesis of Quinazolin-4(3H)-ones through Anodic Oxidation and the Related Mechanistic Studies
2018, Advanced Synthesis and Catalysis
A metal‐free and oxidant‐free method for the one‐pot preparation of quinazolin‐4(3H)‐ones enabled by electrochemical oxidation is described. Together with 2‐aminobenzamides, a variety of aldehydes were successfully applied to an acid‐catalyzed annulation and direct anodic oxidation cascade, affording structurally diverse quinazoline‐4(3H)‐ones in good to excellent yields. Additionally, certain alcohols can be directly applied instead of the corresponding aldehydes to achieve the same final products with the assistance of an electrolysis mediator (TEMPO). The reaction mechanism was carefully examined and the results strongly suggest that the direct and indirect oxidation go through different pathways. As an efficient and environmentally friendly access to a broad range of quinazolin‐4(3H)‐ones, the synthetic utility of this method was demonstrated by gram‐scale operation, as well as the preparation of bioactive mackinazolinone and truncated erlotinib.
Auto-Tandem Catalysis with Ruthenium: From o-Aminobenzamides and Allylic Alcohols to Quinazolinones via Redox Isomerization/Acceptorless Dehydrogenation
2018, Advanced Synthesis and Catalysis
A strategy for the synthesis of quinazolinones via Ru‐catalyzed redox isomerization/acceptorless dehydrogenation was proposed and accomplished. In the presence of a commercially available [(p‐cymene)Cl₂]₂, a range of desirable products were obtained with o‐aminobenzamides and allylic alcohols as starting materials in moderate to high yields. This strategy is attractive due to high atom efficiency, and minimal consumption of chemicals and energy.

View all citing articles on Scopus

View full text

Microwave-assisted one-pot synthesis of 2,3-disubstituted 3H-quinazolin-4-ones

Abstract

Graphical abstract

Section snippets

Acknowledgements

J. Chem. Soc. (C)

J. Org. Chem.

J. Heterocyclic Chem.

Tetrahedron

J. Med. Chem.

J. Org. Chem.

J. Med. Chem.

J. Indian Chem. Soc.

Bull. Soc. Chim. Fr.

Bioorg. Med. Chem. Lett.