Synthesis of phenyl-substituted derivatives of decahydrophenanthridine-1, 7-dione and hexahydro-8-isoquinolone (original) (raw)

Enones with strained double bonds. 3. Cycloadducts from bicyclo[3.3.1]non-1-en-3-one

The Journal of Organic Chemistry, 1979

compound 17, which crystallized from N,N-dimethylformamide: mp 338-340 "C; 40 mg, 8%; NMR 6 7. 48 (m, 4 H), 7.68 (m, 4 H), 7.88 (m, 3 H), 8.04 (s, 1 H), 8.48 (s, 1 H); UVmarCHC's 315 (log 6 5.Anal. Calcd for C24H12:Br2: C, 62.60; H, 2.65; Br, 34.75. Found C, 62.42; H, 27.74; Br, 34.44.

SYNTHESIS OF 3-ARYL-2-BENZYL-1,2-DIHYDROQUINOXALINES THROUGH THE REACTION BETWEEN 1,2-DIAMINO-4,5-DIMETHYLBENZENE AND l,2-DIAMINO-4- METHYLBEZENE WITH 2-BROMO-1,3-DIARYL-1-PROPANONES

Heterocyclic Communications, 2000

Reaction of 1,2-diaminobenzenes (1,4) with substituted 2-bromo-l-aryl-3-phenyl-l-propanones (2a-e) was studied. The structures of 2-benzyl-3-aryl-l H-quinoxalines (3, 5/6) obtained was corroborated by 'H-nmr and mass spectra data. Introduction 1,2-Dihydroquinoxaline derivatives belong to a kind of unexplored compounds owing to their high tendency to oxidation [1], For that, there are few reports about these substances. Besides their fluorescent properties, some dihydroquinoxalines have shown interesting chemiotherapeutic characteristics [2,3], moreover their usefulness like virucides [4]. The investigation on the reaction between ωbromoacetophenones and 4-chloro-and 3,5-dichloro derivatives of 1,2-phenylenediamine let us to elucidate the isomeric composition of the respective products through 'H-nmr and to study the effect of the substituents on the reaction velocity and electronic absorption and emission properties of the obtained products [5]. The reaction of 1,2-phenylenediamines with asymmetric trans-diaroylethylenes afforded specific information about the orientation of the reaction through electronic absorption and mass spectra of the obtained compounds [6]. On the other hand, Orlov et al. reported the synthesis of stable dihydroquinoxalines via the reaction of 1,2-phenylenediamine with 2-bromo-l,3-diaryl-l-propanones [7].

Synthesis of Heterocyclic Compounds, XXXVIII. Five-membered Heterocycles by Cyclization of 3-Benzoyl-4-oxobutanenitriles

Liebigs Annalen der Chemie, 1985

A synthesis of N-benzylidene-2-furanamines 8 by means of cyanide addition to acylchalcones 2, followed by piperidine-catalyzed cyclization in the presence of an aldehyde is reported. The 2-pyrrolones 4 are formed together with the compounds 8. In the absence of an aldehyde no furan is obtained. The intermediate 2-ary1-3-benzoyl-4-0~0-4-phenylbutanenitriles 3 are easily isolated. The N-benzylidene-2-furanamines 9 are obtained from the oxonitriles 5.