Benzo 2-chloro-4-methoxy

The structure of the product obtained by the silver(I) ion catalyzed ring expansion of anti-1-chloro-2,3-benzo-7-azabicyclo[2.2.l]hepta-2,5-diene, formulated tentatively as 1-methoxy-l/f-1-benzazepine,140 has been shown to be 2-methoxy-6,7-benzo-l-azabicyclo[3.2.0]hept-3-ene... 

There are several new methodologies based on the Julia olefination reaction. For example, 2-(benzo[t/Jthiazol-2-ylsulfonyl)-j -methoxy-i -methylacetamide 178, prepared in two steps from 2-chloro-iV-methoxy-jV-methylacetamide, reacts with a variety of aldehydes in the presence of sodium hydride to furnish the ajl-unsaturated Weinreb amides 179 <06EJOC2851>. An efficient synthesis of fluorinated olefins 182 features the Julia olefination of aldehydes or ketones with a-fluoro l,3-benzothiazol-2-yl sulfones 181, readily available from l,3-benzothiazol-2-yl sulfones 180 via electrophilic fluorination <06OL1553>. A similar strategy has been applied to the synthesis of a-fluoro acrylates 185 <06OL4457>. 

Such reactions have also been carried out on benzofurans carrying benzyl, fluoro, chloro, bromo, methoxy, cyano, and phenyl groups in the benzo ring. Substitution in the stilbene part of the molecule can also be obtained by the use of Schiff s bases derived from differing benzal-dehydes.26,28,29... 

Bromination of (VI) gives the dibromo derivative which, on refluxing in methanol, followed by dehydrobromination with KOH in refluxing methanol, gave lo-methoxy-4H-benzo- [ 4,5] -cyclohepta- [l,2-b] --thiophene-4-one (IX). This compound was condensed with the magnesium derivative of 4-chloro-l-methyl-piperidine in tetrahydrofurane, and the resulting lo-methoxy-4-(l-methyl-4-piperidyl)-4H-benzo[4,5]--cyclohepta-[1,2-b]-th phene-4-one (X) was finally dehydrated and demethylated with HC1 at 95-loo°C, to give the base of ketotifen (4). 

A mixture consisting of 6-chloro-3-methoxy-5,9-diaza-benzo[c]fluoren-7-one (21 mg), A-methyl-2,2 -diaminodiethylamine (3.3 mg), and K2C03 (10 mg) was suspended in 0.5 ml DMF and stirred 13 hours at 90°C, then concentrated. The residue was purified by chromatography on silica gel using CH2Cl2/methyl alcohol,... 

The preparation of the Step 1 co-reagent, 6-chloro-3-methoxy-5,9-diaza-benzo[c]fluoren-7-one, (II), by Aoyama (1) is illustrated in Eq. 2. The effectiveness of these derivatives, (III), against HCT116 cells is provided in Table 2. 

Illuminati and co-workers have recently reported additional data on the effects of benzo-ring substituents on the rate of methoxy-dechlorination of quinolines, quinoxalines, and cinnolines the accelerations and decelerations reflect the decreases and increases in activation energy. Both 6- and 7-chloro groups increase the rate (by 6- and... 

The synthesis of some novel fluoro-substituted benzo[a]phenothiazines and their nucleosides as possible antimicrobial agents was reported [196]. 6-(2-Methoxy-5-methyl/2-methoxy-4-chloro-5-methyl-anilino)-9-fluoro-5H-b enzo [ a ] phenothiazine-5-ones/thiones, 12H-benzo [ a ] phenothiazine-5-ols, 5-acetoxy-12H-b enzo [ a ] phenothiazines, 5-methoxy-12H-benzo [ a ]phenothia-zines and nucleosides, viz N-(2,3,5-lri-0-bcnzoyl-f>-D-ribofuranosyl)-6-(2-methoxy-5-methyl/2-methoxy-4-chloro-5-methyl-anilino)-9-fluoro-5-acetoxy benzo[a]phenothiazines and 9-fluoro-5-methoxy benzo[a]phenothiazines, were synthesized and tested for their antimicrobial activity. The structures of novel compounds were proposed on the basis of elemental analyses, IR and and 19F NMR studies. 

In contrast, 4,5-dimethyl-2-methoxy-l,3,2-dioxaphospholane reacts sluggishly with ethyl chloroacetate and only ethyl bromoacetate leads to the desired five-membered cyclic phosphonates as mixtures of the racemic and meso isomers. The 2-ethoxy-benzo[l,3,2]dioxaphosphole on reaction with chloro-, bromo-, or iodoacetate at 200-230°C leads to the 2-(ethoxycarbonyl)methyl-2-oxo-benzo[l,3,2]dioxaphosphole in variable yields (42-58%). ... 

Equation (b) shows the interaction of (II) with 4-chloro-l-methylpiperidine to form the intermediate lO-methoxy-4- (l-methyl-4-piperidyl)-4 H-benzo [4, 5] cycloheptal [1, 2-6]-thiophen-4-ol (III). The resulting intermediate (III) finally forms ketotifen with the elimination of one mole each of hydrochloric acid and methanol. 

The 4-hydroxy compound (108) formed on addition of an aryl Grignard reagent to 7-chloro-2-methoxy-3/f-benzo-l,4-diazepine 4-oxide can be dehydrated by heating either with phenyl isocyanate or V,V -dimethylpiperazine. Dehydration with phenyl isocyanate gave the 57/-isomer (109) while heating with V,V -dimethylpiperazine furnished the 3/7-isomer (110). Compound (109) could also be converted into the (110) on heating with V,V -dimethylpiperazine <77ACS(B)70l>. 

Ci8H2iClNa02, 2-(3-(7-Chloro-2-methoxy-10-(benzo[b]-1,5-naphth-yridinyl)amino)propylamino)ethanol, 41B, 350 Ci 8 2 iIN/,02, 1-Nitro-9-(3-dimethylaminopropylamino)-acridine monoiodide, 41B, 351... 

Barhn GB, Davies LP, Harrison PW, Ireland SJ, Willis AC (1996) Imidazo[l, 2-b]pyridazines. XX. Syntheses of some 3-acylaminomethyl-6-(chloro, fluoro, methoxy, methylthio, phenoxy and phenylthio)-2-(phenyl, 4-t-butylphenyl, 4-cyclohexylphenyl, p-naphthyl and styryl) imidazopyridazines and their interaction with central and peripheral-type benzo. Austr J Chem 49 451-462... 

Nucleophilic Substitution, Metallation, and Halogen-Metal Exchange.—Direct nucleophilic displacement of the 7-chloro-group of 7-chloro-3-methyl-benzo[b]thiophen has been achieved. 3-Bromobenzo[b]thiophen was reduced to the 3-deuterio-derivative by the reaction with sodium borodeuteride and palladium chloride. Meisenheimer complexes were formed in the reaction of methoxide ion with 2-methoxy-3-nitro- and 3-methoxy-2-nitrobenzo[b]thiophen. Rate and equilibrium data were determined in methanol at 25 C. On treatment of 2-bromobenzo[b]thiophen with potassium amide in liquid ammonia, bromine migration to the adjacent carbon atom was observed. Considerable evidence for the occurrence of an intermolecular transbromination was obtained. The reaction of 3-bromo-benzo[b]thiophen with piperidine has been reinvestigated and found to give primarily the normal, but also some of the cine-substitution product, which is the only product obtained in the reaction of 2-bromobenzo[b]thiophen. Possible mechanisms for some of these reacticms are suggested. 

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