Etude des conditions D'accés aux 6,11‐dihydro‐5<i>H</i>‐pyrimidino[4,5‐<i>a</i>]carbazoles

Gazengel, Jean-Marie; Lancelot, Jean‐Charles; Rault, Syl­vain; Robba, M.

doi:10.1002/jhet.5570270718

Cited by 9 publications

(2 citation statements)

References 14 publications

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“…1 H NMR spectra were re corded on a Bruker AC 200 spectrometer in DMSO d 6 . The course of the reactions was monitored and the purity of the compounds was checked by TLC on Silufol UV 254 plates in chloroform-methanol (10 : 1) for compounds 1, 2, 4, 6, 7, 9, and 12-14, benzene-methanol (9 : 1) for compounds 5, 8, and 10, and benzene for compound 11.…”

Section: Methodsmentioning

confidence: 99%

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Synthesis and properties of pyrimido[4,5-a]- and pyrido[4,3-a]carbazole derivatives

et al. 2004

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Methods for the synthesis of substituted pyrimido[4,5 a] and pyrido[4,3 a]carbazoles were proposed. Condensation of 2 (dimethylaminomethylene) 6 methyl 2,3,4,9 tetrahydro 1H carbazol 1 one with guanidine and thiourea afforded 2 amino 8 methyl 6,11 dihydro 5H pyrimido[4,5 a]carbazole and 8 methyl 3,5,6,11 tetrahydro 2H pyrimido[4,5 a]carb azole 2 thione, respectively. The reaction of cyano(6 methyl 2,3,4,9 tetrahydro 1H carbazol 1 ylidene)acetamide with dimethylformamide dimethyl acetal gave N (dimethylamino methylene)cyano(6 methyl 2,3,4,9 tetrahydro 1H carbazol 1 ylidene)acetamide. Cycliza tion of the latter yielded 1 cyano 8 methyl 3,5,6,11 tetrahydro 2H pyrido[4,3 a]carb azol 2 one.

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Section: Methodsmentioning

confidence: 99%

“…Structure 5 was completely confirmed by 1 H NMR and MS data (Tables 1, 2). However, compound 5 was not isolated in the analytically pure state; for its unambiguous identifica tion, it was S benzylated to give 2 benzylthio 8 methyl 6,11 dihydro 5H pyrimido[4,5 a]carbazole (6), which was purified without difficulties.…”

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confidence: 99%