Tumorhemmende Wirkstoffe, 12. Mitt. 2‐Ureido‐4(3<i>H</i>)‐pyrimidinone

Kreutzberger, A.; Schimmelpfennig, H.

doi:10.1002/ardp.19813140107

Archiv der Pharmazie

1981

DOI: 10.1002/ardp.19813140107

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Tumorhemmende Wirkstoffe, 12. Mitt. 2‐Ureido‐4(3H)‐pyrimidinone

A. Kreutzberger

H. Schimmelpfennig

Abstract: 34Kreutzberger und Schimrnelpfennig Arch. Pharm. 4'.5'-Dimethoxy-9-methyl-3.7-imino-l.2-benzocycloocten-5-ol-hydrochlorid (21 HCI)4.4 g (16.9 mmol) 20 werden nach der fur die Darstellung von 16 angegebenen Vorschrift mit NaBH, reduziert und aufgearbeitet. Aus ethanolischer Chlorwasserstoffdure wird das Hydrochlorid ausgefallt und aus Ethanol umkristallisiert. Schmp. 248" (subl. ab 2 W , Ethanol); Ausb. 4.8 g(95 %).

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Cited by 11 publications

References 22 publications

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Antineoplastika, 15. Mitt. Butylderivate der 5‐Aminomethylenbarbitursäure

Kreutzberger

1985

Archiv der Pharmazie

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A ntineoplastika 821 6) 4-Benzyloxy-3-oxo-2,2-diphenyl-1,4-thiazinan-5-iminiumchlorid (7Ab) 2 mrnol7b werden in 201111 absol. Ether suspendiert und unter Schiitteln rnit HCI behandelt. Nach 15 rnin trennt man das kristalline Produkt ab und wascht mehrmals mit Ether. Ausb.: 90 %. -Schrnp. 142". (Zers.). -IR: 1755 (C=O) und 1635cm-' (C=N). G3H2,ClN20,S (425.0) Ber.: C 65.0 H 4.98 N 6.6 Gef.: C 65.0 H 5.28 N 6.9. Benzyloxy-2,2-diphenyl-l,4-thiazinan-3,5-dion (10) 2 mmol7Ab werden in 20 ml Ethanol 2 h riickflieaend erhitzt. Man engt anschlieSend i. Vak. ein und stellt zur Kristallisation in den Kiihlschrank. Man erhalt 0.73 g (93 %) farblose Kristalle mit Schmp. 130" (Lit.'): 130"). -IR: 1730 und 1700crn-' (C=O). * *) Als Teil eines Referats vorgetragen im Wissenschaftlichen Kolloquiurn der Universitat Heidelberg, Mai 1984. 0365-6233/85/o9op-o821$ M.M/O 0 VCH Verlagsgescllochaft mbH, D-6940 Wcinhcim, 1985 und Johannes Reisch 0365-6233/85-24 S M.50/0 7) 4-

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Antineoplastika, 15. Mitt. Butylderivate der 5‐Aminomethylenbarbitursäure

Kreutzberger

1985

Archiv der Pharmazie

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ChemInform Abstract: TUMOR INHIBITORY AGENTS. PART 12. 2‐UREIDO‐4(3H)‐PYRIMIDINONES

Kreutzberger¹,

Schimmelpfennig²

1981

Chemischer Informationsdienst

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Selective and Efficient Structural Elaboration of 2‐(Trifluoromethyl)quinolinones

Marull

Schlosser

2003

Eur J Org Chem

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Keywords:Bromine-lithium exchange / Ethyl 4,4,4-trifluoroacetoacetate / Heterocycles / Hydrogen-lithium exchange / RegioselectivityThe acid-catalyzed cyclization-condensation between anilines and ethyl 4,4,4-trifluoroacetoacetate affords 1,4-dihydro-2-trifluoromethyl-4H-4-quinolinones (1), which can easily be converted into 4-bromo-2-(trifluoromethyl)quinolines. These undergo halogen/metal exchange, generating 2-trifluoromethyl-4-quinolyllithiums, when treated with butyllithium, and hydrogen/metal exchange, generating 4-bromo-2-trifluoromethyl-3-quinolyllithiums, when treated with Ethyl 4,4,4-trifluoroacetoacetate, technically manufactured by addition of trifluoroacetyl chloride to ketene, [1] is a most versatile component for condensation and cyclization reactions. From this building block, considerable numbers of 2-(trifluoromethyl)furans, [2] 2,5-dihydro-4-trifluoromethyl-2-furanones, [3] trifluoromethyl-substituted sugars [4,5] or cyclohexenones [6] and 4-trifluoromethyl-2-benzopyranones have been prepared. An even greater variety of five-and six-membered nitrogen heterocycles has also been made available in such a way: 3-(trifluoromethyl)pyrroles, [7,8] 5-(trifluoromethyl)pyrazoles, [9,10] 3-(trifluoromethyl)-5-pyrrolinones, [11Ϫ15] 1,4-dihydro-2,6-bis(trifluoromethyl)pyridines, [16] 2-hetero-substituted 4-trifluoromethyl-6-pyridinones, [17Ϫ19] 2-amino-substituted 4-(trifluoromethyl)pyrimidines [20,21] or -pyrimidones [22Ϫ25] and (trifluoromethyl)quinolinones. [25Ϫ29] The purpose of this report is to draw attention to the synergies which can be exploited when an electronegative [a]

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Tumorhemmende Wirkstoffe, 12. Mitt. 2‐Ureido‐4(3H)‐pyrimidinone

Cited by 11 publications

References 22 publications

Antineoplastika, 15. Mitt. Butylderivate der 5‐Aminomethylenbarbitursäure

Antineoplastika, 15. Mitt. Butylderivate der 5‐Aminomethylenbarbitursäure

ChemInform Abstract: TUMOR INHIBITORY AGENTS. PART 12. 2‐UREIDO‐4(3H)‐PYRIMIDINONES

Selective and Efficient Structural Elaboration of 2‐(Trifluoromethyl)quinolinones

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