Environmentally friendly methods were applied to prepare quinazolin-4(1H)-one derivatives in either aqueous or solventless medium from anthranilamide and a number of ketones.With dialkyl-substituted ketones, acetophenone and cycloalkanones, the ring closure proceeded smoothly under either aqueous or solventless conditions.With poorly water-soluble cycloalkanones, the ring closure was carried out under mechanochemical ball-milling conditions, in the presence of molecular iodine as catalyst.The environmentally friendly protocols applied resulted in the corresponding quinazolinones in quantitative yields.

Environmentally Friendly

10.3998/ark.5550190.p008.717

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Citations (15)

CCDC 187029: Experimental Crystal Structure Determination

The Cambridge Structural Database (2003)

Ferenc Miklós Pál Sohår Antal Csámpai R. Sillanpaa M. Peter

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

Crystal (programming language)

10.5517/cc68m68

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Citations (0)

Preparation of Heterocycles by Microwave-Induced Retro Diels-Alder Reaction

Letters in Organic Chemistry (2006)

Ferenc Miklós Géza Stájer Ferenc Fülöp

Pyrimidinone, thioxopyrimidinone, pyrimido[2,1-a]phthalazinone and [1,3]oxazino[2,3-a] isoindolone were obtained by means of microwave-assisted [4+2] cycloreversion. The microwave heating of the parent norbornene or oxanorbornene fused compounds in a solvent with a medium or large loss factor generates retro Diels-Alder products in excellent yield and high purity. Keywords: Microwave, retro Diels-Alder reaction, N,N-, O,N-heterocycles

Diels–Alder reaction

Norbornene

Microwave heating

10.2174/157017806779468086

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Citations (12)

diexo-3-Aminonorbornane-2-carboxylic Acid as Highly Applicable Chiral Source for the Enantioselective Synthesis of Heterocycles

Synlett (2008)

Ferenc Fülöp Ferenc Miklós Enikő Forró

Diastereomers of tetracyclic pyrrolopyrimidine derivatives 2 and 3 were prepared in a three-step domino reaction from diexo-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide with levulinic acid or p-toluoylpropionic acid. When subjected to a microwave-mediated retro-Diels-Alder reaction, these tetracycles furnished bicyclic pyrrolo[1,2-a]pyrimidines through the loss of cyclopentadiene. When enantiomeric diexo-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide was used, the products were enantiomeric heterocycles with ee >99%, demonstrating that the title compound is an excellent chiral source.

Diastereomer

Cyclopentadiene

Enantiomeric excess

Carboxamide

Ene reaction

10.1055/s-2008-1077793

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Citations (22)

Synthesis and Structure of Methanobenzocyclooctene Derivatives.

Acta chemica Scandinavica/Acta chemica Scandinavica. B, Organic chemistry and biochemistry/Acta chemica Scandinavica. A, Physical and inorganic chemistry/Acta chemica Scandinavica. Series B. Organic chemistry and biochemistry/Acta chemica Scandinavica. Series A, Physical and inorganic chemistry (1998)

Ferenc Miklós Ferenc Csende Géza Stájer Pál Sohår Reijo Sillanpää

10.3891/acta.chem.scand.52-0322

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Citations (5)

CCDC 922681: Experimental Crystal Structure Determination

The Cambridge Structural Database (2013)

Ferenc Miklós István M. Mándity Reijo Sillanpää Ferenc Fülöp

10.5517/cczz3xy

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Citations (0)

ChemInform Abstract: Application of a Ball Milling Technique for the Condensation of Anthranilic Hydrazides with Aromatic Aldehydes Towards 4‐Quinazolinone Derivatives.

ChemInform (2015)

Tibor Magyar Ferenc Miklós László Lázár F. FUELOEP

Abstract The condensation of anthranilic hydrazide with aldehydes in absence of any catalyst leads to corresponding hydrazones or dihydroquinazolin‐4(1H)‐one derivatives depending on the educt ratio or the hydrazide structure.

Quinazolinone

Anthranilic acid

Condensation reaction

10.1002/chin.201526224

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A Simple Green Protocol for the Condensation of Anthranilic Hydrazide with Cyclohexanone and N‐Benzylpiperidinone in Water

Journal of Heterocyclic Chemistry (2014)

Ferenc Miklós Ferenc Fülöp

An environmentally benign condensation of anthranilic hydrazide with cyclohexanone or N ‐benzylpiperidin‐4‐one in aqueous medium has been developed for the synthesis of benzoylhydrazones A. The thermal rearrangements of hydrazones A yielded 3′‐aminospiro‐quinazolinones B. When A or B was reacted repeatedly with cyclohexanone or N ‐benzylpiperidin‐4‐one, spiroquinazoline‐hydrazones C were formed. From aqueous suspensions, products could be isolated in high purity by simple filtration.

Anthranilic acid

10.1002/jhet.1844

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Citations (4)