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1.
G. Zigeuner Ch. Knopp A. Fuchsgruber 《Monatshefte für Chemie / Chemical Monthly》1970,101(6):1827-1828
Dihydro-6-styryl-2(1H)-pyrimidinones (-thiones) (1) give with acids hexahydro-2(1H)-quinazolinones (-thiones) (2b). The structure2 b is proved by synthesis. 相似文献
2.
G. Zigeuner G. Duesberg E. Fuchs F. Paltauf 《Monatshefte für Chemie / Chemical Monthly》1970,101(6):1794-1796
Dihydro-6-styryl-2(1H)-pyrimidinones (-thiones) react with 1,3-dinucleophilic compounds (phenoles, cyclic diketones) to derivatives of spiro[1]benzopyran-2,4′-pyrimidine. 相似文献
3.
G. Zigeuner W. Adam A. Frank H. Reuther 《Monatshefte für Chemie / Chemical Monthly》1970,101(5):1403-1414
Zusammenfassung Dihydro-4,4,6-trimethyl-2(1H)-pyrimidinone reagieren mit Formaldehyd und sekundären bzw. primären Aminen zu 6-Dialkylaminoäthylidentetrahydro-2(1H)-pyrimidinonen bzw. Hexahydro-2(1H)-pyrido[4,3-d]Pyrimidinonen. Mit Succindialdehyd bzw. Glutardialdehyd und primären Aminen entstehen 5,7-Äthanohexahydro-2(1H)-pyrido[4,3-d]pyrimidinone bzw. Tetrahydro-6,8-propano-6H-pyrimido[1,6-c]pyrimidin-1(2H)-one. Die 6-Dialkylaminoäthylidentetrahydro-2(1H)-pyrimidinone geben mit Phenolen Tetrahydrospiro([1]benzopyran-2,4(1H)-pyrimidin)-2(3H)-one, mit cycl. -Dicarbonylverbindungen Hexahydrospiro([1]benzopyran-2,4(1H)-pyrimidin)-2,5(3H, 6H)-dione bzw. Tetrahydrospiro(2H,5H-pyrano[3,2-c][1]benzopyran-2,4(1H)-pyrimidin)-2(3H),5-dione bzw. mit Malonestern -(Tetrahydro-4,4-dimethyl-2-oxo-6-pyrimidyl)-äthylmalonester.Zusammenfassung Dihydro-4.4.6-trimethyl-2(1H)-pyrimidinones react with formaldehyde and sec. and prim. amines resp. to 6-dialkylaminoethylidentetrahydro-2(1H)-pyrimidinones and hexahydro-2(1H)-pyrido[4.3-d]pyrimidinones, resp. succindialdehyde and glutaraldehyde with primary amines give 5.7-ethanohexahydro-2(1H)-pyrido[4.3-d]pyrimidinones and tetrahydro6.8-propano-6H-pyrimido[1.6-c]pyrimidin-1(2H)-ones, resp. 6-Dialkylaminoethylidentetrahydro-2(1H)-pyrimidinones react with phenols to tetrahydrospiro([1]benzopyran-2.4(1H)-pyrimidin)-2(3H)-ones, with cyclic -dicarbonyl compounds to hexahydrospiro([1]benzopyran-2.4 (1H)-pyrimidin)-2,5 (3H), 6H)-diones and tetrahydrospiro(2H,5H-pyrano[3.2-c][1]benzopyran-2.4(1H)-pyrimidin)-2(3H),5-diones, resp., with malonates -(tetrahydro-4.4-dimethyl-2-oxopyrimidyl-6)-ethylmalonates.
Herrn Prof. Dr.F. Kuffner zum 65. Geburtstag gewidmet. 相似文献
Mannich reaction with dihydro-6-methyl-2(1H)-pyrimidinones
Herrn Prof. Dr.F. Kuffner zum 65. Geburtstag gewidmet. 相似文献
4.
Zusammenfassung Dihydro-4,4,6-trimethyl-2(1H)-pyrimidinone (1) bzw.-thione reagieren mit Schwefel und Morpholin zu Tetrahydro-2-oxobzw.-2-thiono-4,4-dimethylpyrimidin-6-thiocarbonsäuremorpholiden (3); mit Schwefel in Dimethylformamid bzw. Tetramethylharnstoff bilden sich Dihydro-3-thiono-3H-1,2-dithiolo-[4,3—d]pyrimidin-5(4H)-one (5) bzw.-3,5-dithione. Das Dihydro-6-methyl-4-phenyl-2(1H)-pyrimidinon2 bzw.-thion geben mit Schwefel und Tetramethylharnstoff das Dihydro-1-methyl-2-oxo-bzw.-2-thiono-4-phenylpyrimidin-6-trimethylcarboxamidin (7). Methylheterocyclen, wie Chinaldin, werden bei analoger Behandlung in Chinolin-2-thiocarbonsäuredimethylamid usw. übergeführt.
Reaction of sulfur + amines with dihydro-2 (1H)pyrimidinones and-thiones
Dihydro-4,4,6-trimethyl-2(1H)-pyrimidinones (1) and-thiones react with sulfur and morpholine to tetrahydro-2-oxo- and-2-thiono-4,4-dimethylpyrimidine-6-thiocarboxylic acid morpholides (3); with sulfur inDMF or tetramethylurea (TMU) the formation of dihydro-3-thiono-3H-1,2-dithiolo[4,3—d]pyrimidin-5(4H)-ones (5) or-3,5-dithiones, resp. was observed. Dihydro-6-methyl-4-phenyl-2(1H)-pyrimidinone (2) (-thione) with sulfur andTMU yields dihydro-1-methyl-2-oxo- and-2-thiono-4-phenylpyrimidin-6-trimethyl-carboxamidine (7). Methyl substituted heterocycles e.g. quinaldine, are converted under analogous conditions to quinoline-2-thiocarboxylic acid dimethylamide and corresponding compounds. *** DIRECT SUPPORT *** A3615139 00018相似文献
5.
G. Zigeuner H. Brunetti H. Ziegler M. Bayer 《Monatshefte für Chemie / Chemical Monthly》1970,101(6):1767-1787
Zusammenfassung Dihydro-6-methyl-4-phenyl-2 (1H)-pyrimidinone (-thione) (1) reagieren als -Methylalkenylharnstoffe bzw.-thioharnstoffe mit Säuren zu Hexahydro-4,4-methylendi-2(1H)-pyrimidinonen (-thionen) (3), mit Phenolen zu Tetrahydro-6-hydroxyphenyl-2(1H)-pyrimidinonen (-thionen) (2), mit Benzaldehyd zu 6-Styrylverbindungen (1 d, e, g) und mit ,-ungesättigten Ketonen zu Tetrahydro-2(1H)-chinazolinonen (7). Aus 1,5-Diphenyl-1,4-pentadien-3-on und Harnstoffen, Thioharnstoffen bzw. Ammonrhodanid entstehen Diphenyl-1,3,7,9-tetraazaspiro-5,5-undecan-2,8-dione (9) bzw. Hexahydrotriphenyl-6-cinnamoyl-2(1H)-chinazolinthione (10). Hexahydro-6-benzoyl-bzw.-6-cinnamoyl-2(1H)-chinazolinone (-thione) (10) bilden sich allgemein bei Einwirkung von ,-ungesättigten Ketonen auf Dihydro-4-phenyl-6-styryl-2(1H)-pyrimidinone (-thione) (1 d, e, g).
Heterocycles, XXVII: Dihydro-6-methyl-(or-6-styryl-)-4-phenyl-2(1H)-pyrimidinones (-thiones); Hexahydro-5-benzoyl-(or-cinnamoyl-)-4,7-diphenyl-2(1H)-quinazolinones (-thiones)
Dihydro-6-methyl-4-phenyl-2(1H)-pyrimidinones (-thiones) (1) react as -methylalkenylureas (-thioureas) with acids to hexahydro-4.4-methylenedi-2(1H)-pyrimidinones (-thiones) (3), with phenols to tetrahydro-6-hydroxyphenyl-2(1H)-pyrimidinones (-thiones) (2), with benzaldehyde to 6-styryl compounds (1 d, e, g) and with ,-unsaturated ketones to tetrahydro-2(1H)-quinazolinones (7).On reacting 1.5-diphenyl-1.4-pentadien-3-one with ureas, thioureas or ammonium thiocyanate, the products formed are diphenyl-1.3.7.9-tetraazaspiro-5.5-undecane-2.8-diones (9) and hexahydrotriphenyl-6-cinnamoyl-2(1H)-quinazolinethiones (10), resp. Hexahydro-6-benzoyl- (or-6-cinnamoyl-)-2(1H)-quinazolinones (-thiones) (10) are formed generally by the action of ,-unsaturated ketones on dihydro-4-phenyl-6-styryl-2(1H)-pyrimidinones (-thiones) (1 d, e, g).相似文献
6.
Dihydro-6-methyl-4-phenyl-2(1H)-pyrimidinthione (1 a) reacts with formaldehyde and amines to 6-(2′-dialkylaminoethyliden)-tetrahydro-resp. 6-(2′-dialkylaminoethyliden)-tetrahydro-5-dialkylaminomethyl-2(1H)-pyrimidinthiones (2) as well as 6-alkyloctahydro-8a-ethoxy- resp. hydroxypyrido-[4,3-d]-pyrimidine-2(1H)-thiones (5). 相似文献
7.
G. Zigeuner A. Frank H. Dujmovits W. Adam 《Monatshefte für Chemie / Chemical Monthly》1970,101(5):1415-1430
Zusammenfassung 6-Alkyl-3,4-dihydro-2(1H)-pyrimidinthione sind als cyclische Alkenylthioharnstoffe der Addition von Phenolen zu 6-Hydroxyphenyltetrahydro-2(1H)-pyrimidinthionen bzw. derMannich-reaktion zu 6-Dialkylaminoäthylidentetrahydro-bzw. 6-Dialkylaminoäthyldihydro-2(1H)-pyrimidinthionen sowie zu Hexahydro-2(1H)-pyrido[4,3—d]pyrimidinthionen zugänglich. 6-Methylderivate können auch in Dihydro-6-styryl-2(1H)-pyrimidinthione bzw., in einem Fall, in ein Hexahydro-4,4-methylendi-2(1H)-pyrimidinthion umgewandelt werden.
Dihydro-2(1H)-pyrimidinethiones (Heterocycles, XXI)
6-Alkyl-3,4-dihydro-2(1H)-pyrimidinethiones (cyclic alkenylthio carbamides) add phenoles to give 6-hydroxyphenyltetrahydro-2(1H)-pyrimidinethiones and undergoMannich reaction, to give 6-dialkylaminoethylidentetrahydro-and 6-dialkylaminoethyldihydro-2(1H)-pyrimidinethiones and hexahydro-2(1H)-pyrido[4,3—d]pyrimidinethiones, resp. 6-Methyl derivatives can also be transformed into dihydro-6-styryl-2(1H)-pyrimidinethiones resp., in one case, into a hexahydro-4,4-methylendi-2(1H)-pyrimidinethione.相似文献
8.
9.
Acylation of the dihydro-2(1H)-pyrimidinones (-thiones) gives 6-(2′-oxoalkyl)dihydro-2(1H)-pyrimidinones (-thiones). 相似文献
10.
《Journal of fluorine chemistry》1988,38(3):335-340
Ph2P-PF2Ph2 has been identified by means 19F- and 31P- NMR spectroscopy as an intermediate product of the disproportionation of Ph2PF. The disproportionation is catalyzed by acids. The reaction mechanism is discussed. PhPF2 disproportionates faster in solution in acetonitrile than neat, forming (PhP)6, instead of (PhP)5. 相似文献
11.
1-Unsubstituted dihydro-6-methyl-2(1H)-pyrimidinethiones undergo an aminolysis in dialkylformamides or methylformamide resp., at higher temperature, and then are rearranged to 4-dialkylaminodihydro-2(1H)-pyridinethiones6 a, b or the 4-methylamino compound6 c. 1-Alkyl- and 1-aryldihydro-6-methyl-2(1H)-pyrimidinethiones1 b, c and tautom, methylenecompounds2b,c resp., react at the same conditions withDMF not only to 4-alkylamino-or 4-arylaminodihydro-2(1H)-pyridinethiones6 c, d but also to 4-dimethylaminodihydro-2(1H)-pyridinethiones6 a. From 3-substituted dihydro-6-methyl-2(1H)-pyrimidinethiones only the 3-aryl compound12 b is converted byDMF to the corresponding dihydro-4-dimethylamino-1-phenyl-2(1H)-pyridinethione14. Also 4-alkylamino- and 4-arylaminodihydro-2(1H)-pyridones18a, b are formed by heating inDMF at 230°C from 1-alkyl- and 1-aryldihydro-2(1H)-pyrimidinones15b, c and of methylene compounds16b, c resp. 2-Methylimino- and 2-phenyliminodihydro-1,3-thiazinethiones19a, b react inDMF viaDimrothrearrangement to the corresponding 1-alkyl- and 1-phenyl-dihydro-2(1H)-pyrimidinethiones1 b, 2 b, 1 c, 2 c and further to 4-alkylamino-and 4-arylaminodihydro-2(1H)-pyridinethiones6 c, d. 相似文献
12.
13.
4,6-Dimethyl-1-phenyl-2(1H)-pyrimidinone (I) was treated with alkyl halides in the presence of sodium hydride at low temperature to afford only C-6 alkylated products III and IV in good yields. Further, the mono-, IIIa-d, and di-alkylated 2(1H)-pyrimidinones IVa-d were selectively obtained by changing the amount of alkyl halides. 相似文献
14.
Ying Peng Huo Xu Qiu Wei Yan Shao Lin Kun An Xian Zhang Bu Lian Quan Gu 《中国化学快报》2009,20(11):1291-1295
Series of new 2-aryl-6-styryl-2,3-dihydropyridin-4(1H)-one derivatives were synthesized in acceptable to good yields by treatment of the curcuminoids with aqueous ammonia,the mechanism was proposed.By modification of the primary products,total 13 new compounds were obtained.The structures of all products were elucidated by spectroscopy analysis including HR-MS,~1H NMR and ~(13)C NMR. 相似文献
15.
G. Gübitz R. Wintersteiger A. Fuchsgruber Prof. Dr. G. Zigeuner 《Monatshefte für Chemie / Chemical Monthly》1977,108(2):381-386
Cyclic ketones react with -aminocrotonamide in inert solvents to 4-methyl-1,5-diazaspiroalken-2-ones (4 a, 4 b, 4 c, resp.). The structure of the compounds is confirmed by their reactivity as well as by their UV, IR, NMR and mass spectra. 相似文献
16.
Novakov I. A. Orlinson B. S. Navrotskii M. B. 《Russian Journal of Organic Chemistry》2009,45(2):316-317
Russian Journal of Organic Chemistry - 相似文献
17.
18.
19.
Prof. Dr. Friedrich Asinger Alfons Saus E. Fichtner H. -J. Gräber W. Leuchtenberger 《Monatshefte für Chemie / Chemical Monthly》1975,106(6):1449-1460
2H-Imidazole-4(3H)-thiones (a), available from methyl alkyl and methyl aryl ketones with sulfur and ammonia, react via their corresponding N-sodium compounds or in presence of tert. amines with alkyl and aryl carboxylic acid chlorides to give the corresponding intensely coloured (orange to violett) cryst. 3-acyl-2H-imidazole-4(3H)-thiones4 a-q and6–26. With dicarboxylic acid dichlorides the colourless cryst. N,N′-diacyl-bis-3-imidazoline-5-thiones5 a-d and27–32 are obtained. With carbamic acid chlorides and chloroformic acid esters the corresponding urea (33–35) and urethane derivatives36, 37 are formed. In an analogous way 2H-imidazol-4(3H)-ones react with acid chlorides to 3-acyl-2-imidazol-4(3H)-ones (44–50), which can also be obtained by treating the corresponding 3-acyl-2H-imidazole-4(3H)-thione with KMnO4. 相似文献