Dibenz properties

H-Dibenz[6,/]azepine, 10,11-dihydro-acylation, 7, 511 alkylation, 7, 511 amination, 7, 512 lithiation, 7, 528 PE spectrum, 7, 502 pharmacological properties, 7, 546 reactions... 

H-Dibenz[6,/]azepine-5-carboxamide pharmacological properties, 7, 546 Dibenz[6,e]azepine-6,11-dione, 10-amino-reactions, 7, 526 Dibenz[6,e]azepinediones intramolecular nucleophilic substitution, 7, 516 synthesis, 7, 531 Dibenz[6,e]azepine-5,11-diones epoxides, 7, 515 reduction, 7, 525... 

Dibenz[6,/]oxepin, 10,11-dihydro-applications, 7, 590 Dibenz[c,e]oxepin, dihydro-conformational interchange, 7, 549 Dibenz[6,/]oxepinylpiperazine, 10,11-dihydro-properties, 7, 590 Dibenz[6,g]oxocin synthesis, 7, 669... 

The central C-C double bond of dibenz[, /]oxepin displays the properties of an activated aromatic system and undergoes substitution reactions. Nitration and acid-catalyzed dcutcration gives the dibenzo[i>,/]oxepins 1 with the respective substituent in position 10.161... 

Bis(bromomethyl)-5//-dibenz[/), / ]azepines, e.g. 12, prepared by free-radical bromination of the 10,11-dimethyl compound with yV-bromosuccinimide, on treatment with a primary alkyl-amine followed by alkaline hydrolysis, yield l,2,3,8-tetrahydrodibenzo[. /]pyrrolo[3,4-<7]-azepines, e.g. 13, which possess useful pharmacological properties.91,163... 

A second vital observation was made when Mayneord, a physicist, joined in the research effort and decided to examine the conspicuous fluorescence of the many carcinogenic distillates present in Kennaway s laboratory. He found that most of the carcinogenic tars exhibited a common fluorescence spectrum (X 400, 418 and 440 nm) but, in subsequent studies with Hieger, none of the hydrocarbons available at that time exhibited these spectral characteristics (7 ). The spectrum of benz[a]anthracene was found to be similar to, but of longer wavelength than, that of the carcinogenic preparations but this similarity directed Kennaway s attention to Clar s report of the synthesis of dibenz[a hjanthracene (10). Tumors were obtained when this hydrocarbon was repeatedly painted on to mice and thus it was established that the properties necessary to elicit tumors in animals were contained within the structure of a single pure chemical compound (11). 

Nucleophilic Trapping of Radical Cations. To investigate some of the properties of Mh radical cations these intermediates have been generated in two one-electron oxidant systems. The first contains iodine as oxidant and pyridine as nucleophile and solvent (8-10), while the second contains Mn(0Ac) in acetic acid (10,11). Studies with a number of PAH indicate that the formation of pyridinium-PAH or acetoxy-PAH by one-electron oxidation with Mn(0Ac)3 or iodine, respectively, is related to the ionization potential (IP) of the PAH. For PAH with relatively high IP, such as phenanthrene, chrysene, 5-methyl chrysene and dibenz[a,h]anthracene, no reaction occurs with these two oxidant systems. Another important factor influencing the specific reactivity of PAH radical cations with nucleophiles is localization of the positive charge at one or a few carbon atoms in the radical cation. 

Dibenz[6,/][ 1,4]oxazepines, which have intense lachrymatory and skin irritant properties, can be prepared in high yield by the Bischler-Napieralsky-type cyclization of N- 2-phenoxyphenyl)formamides (76JCS(P1)1279>. 

Analytical Properties Resolution of several enantiomers of polycyclic aromatic hydrocarbons, for example, chrysene 5,6-epoxide, dibenz[a,h]anthracene 5,6-epoxide, 7-methyl benz[a]anthracene 5,6-epoxide resolution of barbiturates, mephenytoin, benzodiazepinones, and succinimides direct separation of some mono-ol and diol enantiomers of phenanthrene, benz[a]anthrene, and chrysene ionically bonded to silica gel, this phase provides resolution of enantiomers of c/s-dihydroidiols of unsubstituted and methyl- and bromo-substituted benz[a]anthracene derivatives having hydroxyl groups that adopt quasiequatorial-quasiaxial and quasiaxial-quasiequatorial conformation Reference 31-35... 

FIGURE 12.8. Chemical stmcture and physicochemical properties of dibenz(b,f)-l 4-oxazepine (CR). 

Boyd and co-workers interest in the properties of arene oxide metabolites has led them to undertake investigations into the synthesis and isomerization of such compounds (e.g., dibenz[ , ]anthracene 3,4-oxide 27, phenanthrene 3,4-oxide 28, triphenylene 1,2-oxide 29, and dibenz[ ,f]anthracene 1,2-oxide 30 (Figure 4)) <2001J(P1)1091>. 

Desipramine Hydrochloride, U5P. The structure and caliciit properties of desipramine hydrochloride, 10,11 -dihy-dro-iV-methyl-5H-dibenz b/ a/epine-5-propanamine mono-bydrochloride. S-(3-mclhylaminopropyl)-IO,l l-dihydro-5/y-diben/. b azepine hydrochloride (Norpramin, Perto-frane). arc discussed under the heading, Imipramine, above,. mnng tricyclics, desipramine would be considered when few iinticholincrgic effects or a low level of sedation arc important. It is a SNERI. ... 

Being interested here in the volatile components of coffee aroma, we shall arbitrarily limit the list of the aromatic hydrocarbons to tricyclic structures. The higher fused polycyclic hydrocarbons (fluoranthene [206-44-0], pyrene [129-00-0], chrysene [218-01-9], benz[ ]anthracene (1,2-benzanthracene) [56-55-3], benz[< ]acephenanthrylene (3,4-benzofluoranthene) [205-99-2], benzo[ ]pyrene (3,4-benzopyrene, 3,4-BP) [50-32-8], benzo[e]pyrene (1,2-benzopyrene) [192-97-2], perylene [198-55-0], benzo[g,/i,/]perylene (1,12-benzopyrene) [191-24-2], and dibenz[ ,//]anthracene (1,2,5,6-dibenzanthracene) [53-70-3]) cannot be considered as a part of the aroma. However, as some of these, specially benzo[o pyrene, are known for carcinogenic properties, they have been particularly analyzed in food subject to roasting or smoke-curing. 

In the 1979 Surgeon General s report (4005), the aza-arenes dibenz[a,/i]acridine, dibenz[a,y ]acridine, 7//-dibenzo[c,g] carbazole, quinoline, and alkylated quinolines in CSC were discussed but not the presence or properties of the V-heterocyclic amines identified in tobacco smoke. 

CHEMICAL PROPERTIES can be hydrogenated to the octadecahydro derivative can be oxidized by chromic acid to dibenz(a,h)anthra-7,14quinone, and to anthraquinone-1,2,5,6-tetracarboxylic acid incompatible with strong oxidizers... 

Benes J, Parada A, Figueiredo AA, et ai. Anticonvulsant and sodium channel-blocking properties of novel 10,11-dihydro-5H-dibenz[b,f]azepine-5-carboxamide derivatives. J Med Chem 2000 42 2582-2587. 

The drug-metabolising properties of skin are considerable. It is reasonable therefore to expect that not only the parent compound, but also its metabolic product, or breakdown product might be responsible for sensitisation. An example seems to be provided by the thiadiazine antifungal and skin-care agent, dibenz-thione. While there is evidence that dibenzthione itself can sensitise skin, it has been shown that a hydrolytic product of this compound, benzisothiocyanate, may also be responsible for some cases of sensitisation (Behrbohm and Zschunke 1965 WuRBACH and Schubert 1976). 

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