Microwave-Assisted Synthesis of Quinazolines and Quinazolinones: An Overview

Overview

Journal Front Chem

Specialty Chemistry

Date 2020 Dec 7

PMID 33282829

Citations 9

Authors

Leyla Mohammadkhani

Majid M Heravi

Affiliations

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Abstract

Microwave irradiation (MWI), as a unique, effective, sustainable, more economic, and greener source of energy compared to conventional heating, is applied in different organic transformations to result in the rapid formation of desired compounds due to thermal/kinetic effects. In this review, we try to underscore the applications of microwave irradiation (MWI) in the synthesis of quinazoline and quinazolinone derivatives that have been achieved and reported on in the last two decades.

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References

Giri R, Thaker H, Giordano T, Williams J, Rogers D, Sudersanam V . Design, synthesis and characterization of novel 2-(2,4-disubstituted-thiazole-5-yl)-3-aryl-3H-quinazoline-4-one derivatives as inhibitors of NF-kappaB and AP-1 mediated transcription activation and as potential anti-inflammatory agents. Eur J Med Chem. 2008; 44(5):2184-9. DOI: 10.1016/j.ejmech.2008.10.031. View

Corbet J, Mignani G . Selected patented cross-coupling reaction technologies. Chem Rev. 2006; 106(7):2651-710. DOI: 10.1021/cr0505268. View

Sheu J, Hung W, Wu C, Lee Y, Yen M . Antithrombotic effect of rutaecarpine, an alkaloid isolated from Evodia rutaecarpa, on platelet plug formation in in vivo experiments. Br J Haematol. 2000; 110(1):110-5. DOI: 10.1046/j.1365-2141.2000.01953.x. View

Heravi M, Ghavidel M, Mohammadkhani L . Beyond a solvent: triple roles of dimethylformamide in organic chemistry. RSC Adv. 2022; 8(49):27832-27862. PMC: 9084326. DOI: 10.1039/c8ra04985h. View

Ghosh P, Ganguly B, Das S . C-H functionalization of quinazolinones by transition metal catalysis. Org Biomol Chem. 2020; 18(24):4497-4518. DOI: 10.1039/d0ob00742k. View

Li W, Zhang J . Synthesis of Heterocycles through Denitrogenative Cyclization of Triazoles and Benzotriazoles. Chemistry. 2020; 26(52):11931-11945. DOI: 10.1002/chem.202000674. View

Wakeling A, Guy S, Woodburn J, Ashton S, Curry B, Barker A . ZD1839 (Iressa): an orally active inhibitor of epidermal growth factor signaling with potential for cancer therapy. Cancer Res. 2002; 62(20):5749-54. View

Correa A, Garcia Mancheno O, Bolm C . Iron-catalysed carbon-heteroatom and heteroatom-heteroatom bond forming processes. Chem Soc Rev. 2008; 37(6):1108-17. DOI: 10.1039/b801794h. View

Xuan J, He X, Xiao W . Visible light-promoted ring-opening functionalization of three-membered carbo- and heterocycles. Chem Soc Rev. 2020; 49(9):2546-2556. DOI: 10.1039/c9cs00523d. View

10.

Gopalaiah K, Saini A, Devi A . Iron-catalyzed cascade reaction of 2-aminobenzyl alcohols with benzylamines: synthesis of quinazolines by trapping of ammonia. Org Biomol Chem. 2017; 15(27):5781-5789. DOI: 10.1039/c7ob01159h. View

11.

Valizadeh H, Heravi M, Amiri M . Unexpected synthesis of N-methylbenzo[d]isoxazolium hydroxides under microwave irradiation conditions. Mol Divers. 2009; 14(3):575-9. DOI: 10.1007/s11030-009-9189-x. View

12.

Heravi M, Ranjbar L, Derikvand F, Alimadadi B, Oskooie H, Bamoharram F . A three component one-pot procedure for the synthesis of [1,2,4]triazolo/benzimidazolo-quinazolinone derivatives in the presence of H6P2W18O(62).18H2O as a green and reusable catalyst. Mol Divers. 2008; 12(3-4):181-5. DOI: 10.1007/s11030-008-9086-8. View

13.

Portela-Cubillo F, Scott J, Walton J . 2-(Aminoaryl)alkanone O-phenyl oximes: versatile reagents for syntheses of quinazolines. Chem Commun (Camb). 2008; (25):2935-7. DOI: 10.1039/b803630f. View

14.

Johansson Seechurn C, Kitching M, Colacot T, Snieckus V . Palladium-catalyzed cross-coupling: a historical contextual perspective to the 2010 Nobel Prize. Angew Chem Int Ed Engl. 2012; 51(21):5062-85. DOI: 10.1002/anie.201107017. View

15.

Foucourt A, Hedou D, Dubouilh-Benard C, Desire L, Casagrande A, Leblond B . Design and synthesis of thiazolo[5,4-f]quinazolines as DYRK1A inhibitors, part I. Molecules. 2014; 19(10):15546-71. PMC: 6270991. DOI: 10.3390/molecules191015546. View

16.

Guo X, Gu D, Wu Z, Zhang W . Copper-catalyzed C-H functionalization reactions: efficient synthesis of heterocycles. Chem Rev. 2014; 115(3):1622-51. DOI: 10.1021/cr500410y. View

17.

Sreenivas D, Ramkumar N, Nagarajan R . Copper-mediated domino synthesis of pyrimido[4,5-b]carbazolones via Ullmann N-arylation and aerobic oxidative C-H amidation. Org Biomol Chem. 2012; 10(17):3417-23. DOI: 10.1039/c2ob07179g. View

18.

Liu J, Wang Y, Zhang J, Yang J, Mou H, Lin J . Phosphatase CDC25B Inhibitors Produced by Basic Alumina-Supported One-Pot Gram-Scale Synthesis of Fluorinated 2-Alkylthio-4-aminoquinazolines Using Microwave Irradiation. ACS Omega. 2018; 3(4):4534-4544. PMC: 6130795. DOI: 10.1021/acsomega.8b00640. View

19.

Wolfe J, Rathman T, Sleevi M, Campbell J, Greenwood T . Synthesis and anticonvulsant activity of some new 2-substituted 3-aryl-4(3H)-quinazolinones. J Med Chem. 1990; 33(1):161-6. DOI: 10.1021/jm00163a027. View

20.

Toure B, Hall D . Natural product synthesis using multicomponent reaction strategies. Chem Rev. 2009; 109(9):4439-86. DOI: 10.1021/cr800296p. View