A catalyst- and solvent-free selective approach to biologically important quinazolines and benzo[g]quinazoline

Kumar, Vipan; Mohan, Chander; Gupta, Manish; Mahajan, Mohinder P.

doi:10.1016/j.tet.2005.01.118

Cited by 65 publications

(31 citation statements)

References 51 publications

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“…Most of them involve the pyrimidine ring closure and require orthosubstituted benzenes, such as anthranilic acids, as starting materials. We and others groups recently reported short and efficient pathways using simple aromatic or heteroaromatic amines as precursors for the synthesis of quinazoline [10][11][12] or quinazolin-4-one derivatives [13,14].…”

Section: Introductionmentioning

confidence: 99%

Catalyst-free synthesis of quinazolin-4-ones from (hetero)aryl-guanidines: application to the synthesis of pyrazolo[4,3-f]quinazolin-9-ones, a new family of DYRK1A inhibitors

et al. 2012

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A small library of heterocycle-fused quinazolin-4-ones was prepared and evaluated as kinase inhibitors. The key step of the two-step process involves the environmental friendly thermolysis of N-ethoxycarbonyl-N'-(hetero) arylguanidines at 130 °C in water. The cyclization is fully regioselective. The most active molecules, 7-(2-hydroxyethylamino)- and 7-(3-hydroxypropylamino)-pyrazolo[4,3-f]quinazolin-9-ones, inhibit DYRK1A and CLK1 at submicromolar concentrations, indicating the potential interest of this new heterocycle in drug design.

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Section: Introductionmentioning

confidence: 99%

Catalyst-free synthesis of quinazolin-4-ones from (hetero)aryl-guanidines: application to the synthesis of pyrazolo[4,3-f]quinazolin-9-ones, a new family of DYRK1A inhibitors

et al. 2012

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“…The reaction proceeds with excellent selectivity for monoarylation ( Scheme 29 ). The resultant N -arylamidines ( 72 ) can serve as precursors for the synthesis of biologically important heterocycles such as imidazoles [44] , benzimidazoles [45] , quinazolines [46] , and quinazolinones [47] . Traditionally, N -arylamidines have been prepared by an additional reaction of aniline to an activated nitrile or amide or by the addition of thioimidic ester [48] .…”

Section: 4-disubstituted Quinazolinesmentioning

confidence: 99%

Synthesis of quinazolines and quinazolinones via palladium-mediated approach

Abdou

AlNeyadi

2015

Heterocyclic Communications

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“…Recently, Mahajan and co-workers developed a solventfree and catalyst free approach towards the selective synthesis of quinazolines and benzo[g]quinazolines [13]. Using a domestic microwave oven, the authors reported the solventfree condensation of N-arylamidines with various aldehydes in the absence of any Lewis acid catalyst.…”

Section: 4-di-substituted Quinazolinesmentioning

confidence: 99%

Microwave-Assisted Synthesis of Bioactive Quinazolines and Quinazolinones

Besson¹,

Chosson

2007

CCHTS

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This paper aims to review recent developments in the synthesis of quinazolines and quinazolinone derivatives under conditions that include the application of microwave heating in the ring forming step. Recently, two reviews on the synthesis and chemistry of natural and synthetic quinazolines and quinazolinones have been published. This review highlights significant examples where microwave heating has been either synthetically enabling or has provided a key advantage over conventional thermal methods. Wherever possible, this review will focus on chemistry carried out using monomode systems and well-designed type of instrumentation. The review is grouped according to the main heterocycle types in order of increasing complexity; commencing with quinazolines and their derivatives. The microwave-assisted synthesis of quinazolines and quinazolinones will be classified and based on the substitution patterns of the ring system. Syntheses of heterocyclic systems of particular biological or commercial interest are emphasized.

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A catalyst- and solvent-free selective approach to biologically important quinazolines and benzo[g]quinazoline

Cited by 65 publications

References 51 publications

Catalyst-free synthesis of quinazolin-4-ones from (hetero)aryl-guanidines: application to the synthesis of pyrazolo[4,3-f]quinazolin-9-ones, a new family of DYRK1A inhibitors

Catalyst-free synthesis of quinazolin-4-ones from (hetero)aryl-guanidines: application to the synthesis of pyrazolo[4,3-f]quinazolin-9-ones, a new family of DYRK1A inhibitors

Synthesis of quinazolines and quinazolinones via palladium-mediated approach

Microwave-Assisted Synthesis of Bioactive Quinazolines and Quinazolinones

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