Naphtho 1-oxid

Azete, trisdimethylamino-isolation, 7, 278 Azetes, 7, 237-284, 278-284 benzo fused, 7, 278 benzodiazepine fused applications, 7, 284 fused ring, 7, 341-362 structure, 7, 360 2,3-naphtho fusion, 7, 278 reactivity, 7, 279 structure, 7, 278 synthesis, 7, 282-283 Azetidine, acylring expansion, 7, 241 synthesis, 7, 246 Azetidine, 3-acyl-irradiation, 7, 239 synthesis, 7, 246 Azetidine, N-acyl-synthesis, 7, 245 Azetidine, alkyl-synthesis, 7, 246 Azetidine, 3-alkylthio-synthesis, 7, 246 Azetidine, 3-amino-synthesis, 7, 246 Azetidine, N-amino-oxidation, 7, 241 synthesis, 7, 246 Azetidine, aryl-synthesis, 7, 246... 

Naphtho[l, 2-c]furazans electrophilic reactions, 6, 410 synthesis, 6, 418 Naphtho[l, 2-c]furoxans eleetrophilic reactions, 6, 410 3-Naphthoic acid, 2-hydroxy-l-(2-thiazolylazo)-analytical uses, 6, 328 Naphtho[ 1,2-h]imidazoles oxidation, 5, 405... 

H-Naphtho[2,3-h]pyran, 5,10-diacetoxy-2-methyl-oxidation, 3, 670 Naphtho[2,3-c]pyran synthesis, 3, 770... 

Some internal oxidation-reduction reactions have been reported with the bisulfite adducts of naphtho[l,2-c]furoxan " and some... 

Octyl Alcohol.—This is the primary normal alcohol of the formula CH3(CH2)gCH20H. It has an odour recalling that of opoponax, and is useful in the blending of perfumes of this type. It boils at 196° to 197°, and has a specific gravity 0"8278. It yields octyl aldehyde on oxidation, whose naphtho-cinchoninic acid compound melts at 234°. 

Meinwald and coworkers71 studied the chemistry of naphtho[l, 8-bc]thiete and its S-oxides. The reaction of the sulphone 2 with LAH (equation 29) is of particular and direct relevance to this section since it is different from the reductions that have been discussed thus far, because the major reaction pathway is now cleavage of an S—C bond, rather than a deoxygenation of the sulphur atom. The major product (equation 29) was isolated in 65% yield two minor products accounted for a further 15% yield. One of the minor products is 1-methylthionaphthalene and this was most probably produced by an initial reduction of the strained 1,8-naphthosulphone, 2, to the thiete, which was then cleaved to the thiol and subsequently methylated. Meinwald also showed71 that the thiete was subject to cleavage by LAH as well as that both molecules were susceptible to attack and cleavage by other nucleophiles, notably methyllithium. These reactions are in fact very useful in attempts to assess a probable mechanism for the reduction of sulphones by LAH and this will be discussed at the end of this section. 

In 2-Oxo-2,3-dihydro-(naphtho-[l,2-e]-l,2,4-triazin)-l-oxiden werden die N-oxid-Gruppen durch Athanol schnell und in guten Ausbeuten reduziert. Dagegen werden die... 

Dinitro-phenanthren gibt in einem Gemisch von Athanol, DMF und Wasser (Leitsalz Kaliumnitrat) an Quecksilber nur wenig Naphtho-[l,8,7-c,d,e]-cinnoIin (16% d.Th.) und dessen N-Oxid (12% d.Th.)4. 

The oxidation of benzo[( ]thiophene by strains of pseudomonads produces the sulfoxide that undergoes an intramolecular Diels-Alder reaction followed by further transformation to benzo[fc]naphtho[l,2- (]thiophene (Figure 2.2b) (Kropp et al. 1994). 

Rhodococcus sp. Strain WU-K2R A Rhodococcus strain capable of sulfur-specific desulfurization of benzothiophene, naphthothiophene (NT), and some of their alkyl derivatives was reported [35]. The metabolites of BT desulfurization were BT sulfone, benzo[c][l,2]oxanthiin S-oxide, benzo[c][l,2]oxanthiin S,S-dioxide, o-hydroxystyrene, 2,(2 -hydroxyphenyl)ethan-l-al, and benzofuran. The NT metabolites were NT sulfone, 2 -hydroxynaphthyl ethene, and naphtho[2,l-b]furan [35], The exact biochemical pathway was not determined, however, part of the pathway for BT desulfurization was speculated to be similar to Paenibacillus All-2. 

The differing nucleophilicity of acetate and trifluoroacetate anion determines the direction in which naphtho[l,8-b,c]-l,5-dithiocine-l-oxide 59 rearranges on treatment with acetic and trifluoroacetic anhydrides. In both cases the reaction proceeds through formation of a disulfonium dication, but the final products are different. When acetic anhydride is used, the reaction affords the corresponding a-acetylsulfide 60 - a normal product of the Pummerer rearrangement, while trifluoroacetic anhydride causes isomerization with formation of dithioacetal 61 (Scheme 22).87... 

Oxidation of several 1,1-bisphenols 78 with IBD gives spirobenzofuran derivatives of general formula 79 (Eq. 21). This approach, when applied to benzylidine l.l -bisnaphthols 80, leads to a stereospecific cyclization, thereby forming the less hindered naphtho[2,l-fi]furan-2(l//)-spiro-r-(2//)-naphthalene-2 -ones (82) [80JCS(P1)1978,80JCS(P1)1986]. The conversion 80 to 82 probably occurs through intermediate 81 (Scheme 25). 

The naphtho[2,3-d]-l,3-dioxole was oxidized using recombinant E. coli whole cells overexpressing the gene for the naphthalene dioxygenase from Pseudomonas putida G7. The linear carbohydrate fragment was enzymatically formed after ozon-ization of the diol, by chain extension with a dihydroxyacetone fragment in an... 

Benzofuroxans can be prepared by oxidation of o-quinone dioximes with, for example, fer-ricyanide or hypohalite in a process which closely parallels the formation of monocychc furoxans from glyoximes. Its utility is restricted by the availability of the starting materials which are themselves often best made by reduction of the furoxan. However, it is a valuable approach when the parent quinone or its monooxime is accessible by other means. It was, for example, the route originally used for naphtho[l,2-c]furoxan, the first aromatic-fused derivative <1886CB176>, and it is the method of choice for acenaphthofuroxans (11). In other cases oxidation of o-nitroanilines or thermolysis of o-nitroaryl azides are more suitable. 

Castle and co-workers <1996JHC119, 1996JHC185, 1997JHC1597, 1998JHC1441> used 3-chlorothieno [2,3-3]thiophene-2-carbonyl chloride 280 in the synthesis of the appropriate amides, which by oxidative photo-cyclization gave novel polycyclic heterocyclic ring systems thieno[3, 2 4,5]thieno[2,3-f][l,10]phenanthroline 281, thieno[3, 2 4,5]thieno[2,3-f]naphtho[2,iy ]quinoline 282 and thieno[3, 2 4,5]thieno[2,3-f]naphtho[l,2-g]qui-noline 283, thieno[3, 2 4,5]thieno[2,3-f]naphtho[l,2y ]quinoline 284, thieno[3, 2 4,5]thieno[2,3-f]naphtho[l,2 7]-[l,2,4]triazolo[3,4- ]quinoline 286, thieno[3, 2 4,5]thieno[2,3-f]naphtho[l,2-/]tetrazolo[l,5- ]quinoline 288, benzo[ ]thieno[3, 2 4,5]thieno[2,3-f]quinoline 285, benzo /]thieno[3, 2 4,5]thieno[2,3-f]quinoline 287, benzol/] thieno[3, 2 4,5]thieno[2,3-f]tetrazolo[l,5- ]quinoline 289, and benzo[/jthieno[3, 2 4,5]thieno[2.3-f][l,2,4]triazolo[4,3- ]-quinoline 290. 

In dicscm Abschnitt wcrdcn nicht nur Bcnzofurazan-1-oxide, sondern auch anellierte Systeme wie -l-oxid und heteroanellierte Vertreter behandelt. 

Die H-NMR-Spektren anderer heteroanellierter Furazan-l-oxide sind pubhziert worden be-merkenswerterweise erscheint in (Naphtho[l,2-cYurazan)-l-oxid (I) 5 (H-9) gegenuber dem entsprechenden 3-Oxid um 0,5 ppm tiefleldverschoben. 

Der Basispeak im Massenspektrum von [Pg.777]

Es ist offenbar bishcr nicht gelungen, das linear anellierte -l-oxid her-zustellen147. 

Aus 8-Hydroxy-[Pg.791]

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