Benzo -dioxole

H20 (20 ml), CH2Br2 (26 g, 0.15 mol) and Adogen (0.45 g, 1 mmol) are stirred and refluxed briefly under N2. The dihydroxyarene (0.1 mol) and aqueous NaOH are then added dropwise over a period of ca. 2 h. The mixture is stirred and refluxed for a further 1 h. The organic phase is separated and the extracts are washed well with aqueous NaOH (1M) and then with H20 until the washings are neutral. The dried (MgS04) organic phase is evaporated to yield the dioxole [e.g. benzo-1,3-dioxole (76%) from catechol naphtho-[2,3-rf]-1,3-dioxole (82%) from 2,3-dihydroxynaphthalene piperonal (80%) from 2,3-dihydroxybenzaldehyde 4-methylbenzo-1,3-dioxole (86%) from 4-methylcatechol]. 

H fNl F paroxetine 3-(Benzo[1,3]dioxol-5-yloxymethyl)-4-(4-fluoro-phenyl)-piperidine, C19FI2oFN03, MW 329.37, [61869-08-7] headache, migraine (10-50 mg/day for 3-9 months) diabetic neuropathy (40 mg/day for 7 weeks) Black and Sheline, 1995 Sindrup et al., 1990b... 

Benzo-1,3-dioxole and related systems, reactivity of benzene ring in ... 

Fig. 8. Chemical structure of tadalafil (6-benzo[1,3]dioxol-5-yl-2-methyl-2,3,6,7,12, 12a-hexahydro-pyrazino[1, 2 1,6]pyrido[3,4-b]indole-1,4-dione). Cocrystal structure of PDE5 and tadalafil (PDB ID 1UDU) with the interaction with the conserved Gln817 is shown.

Benzodioxol-5-yl) ethyl octyl sulfoxide. See Piperonyl sulfoxide 1 -[5-(1,3-Benzodioxol-5-yl)-1 -oxo-2,4-pentadienyl] piperidine (E,E)- 1,3-Benzodioxol-5-yl-oxo-2,4-pentadienyl piperine 5-Benzo [1,3] dioxol-5-yl-1-piperidin-1-yl-penta-2,4-dien-1-one. See Piperine... 

Benzo [ 1,3] dioxol-5 -yl( l//-indol-3-yl)methyl)-4-hydroxy-2//-chromen-2-one (4ae) ... 

Piperine 5-Benzo[1.3]dioxol-5-yl-l-(l-piperidyl) penta-2,4-dien-1-one 94-62-2... 

Piperonyl butoxide 0 Ouwenling R Resmethrin 3 5-[2-(2-Butoxyethoxy)ethoxymethyl]-6-propyl-benzo [1,3] dioxole 51-03-6... 

Benzo-1.3-dioxole 2.2-dinhosphonic acid f Q.2-Dhenvlenedioxy)methvlenediphosphonic acid1... 

The first few millilitres of distillate is likely to be unreacted benzo-dioxole. This will come over at about 8CTC. The best thing to do here is wait for the temperature to get to about 9CfC and then stop everything, change flasks and start again. Don t allow the reaction flask to heat up while you change flasks, in fact let it cool down a bit - if you don t, you ll know why I said this. 

The reverse trend is observed with (Z)-enolates. The reaction of the lithium enolate of cyclohexanone with ( )-(2-nitroethenyl)benzene gives a 75 25 mixture of the syn- and anti-adducts. In contrast, the same enolate undergoes addition of ( )-5-(2-nitroethenyl)-l,3-benzo-dioxole to give exclusively the yymaddition product in 93% yield2. 

Acetamides, (V-arylalkyl-, 56, 7 5- 2-Acetamidoethyl)-6-acetyl 1,3-benzo-dioxole, 56, 7... 

Hydroxy-3-methoxy-[(2S,3aR,3bS, 6aR,9aR,9bR, 10R,11aR)-3a,3b,6,6a,9a,10,11,11a-octahydro-6a-hydroxy-8,10-dimethyl-11a-(1-methyl-ethenyl)-7-oxo-2-(phenyl-methyl)-7H-2,9p-epoxy-azuleno[5,4-e]-1,3-benzo-dioxol-5-yl]benzeneacetic acid, C37H40O91 Mr 628.71. 

Since the publication of the corresponding chapter in CHEC-II(1996) <1996CHEC-II(3)525>, there have been a large number of developments in the chemistry of 1,3-dioxole systems and these have mainly involved 1,3-benzo-dioxoles 1, 1,3-dioxolanes 2, and the isomeric l,3-dioxolan-2-ones 3 and l,3-dioxolan-4-ones 4. There have been specific reviews on the synthesis of 1,3-dioxolium salts 5 <2002SOS(11)13> and the transformations of the 6,8-dioxabicyclo[3.2.1]octane compounds 6 <2003SL1759>. 

Electrochemical methoxylation has been achieved by anodic oxidation of substituted 1,3-benzo-dioxoles in NaOMe/MeOH saturated with CO2, leading to the 2-methoxy derivatives <85S3i>. 

US patent 6,767,921, Polymorphic forms of fasidotril, their methods of preparation and pharmaceutical compositions comprising them [115]. The subject of this invention are polymorphic Forms I, II, III, IV of benzyl (S,S)-2-(2-acetylsul-phanylmethyl-3-benzo[l,3]dioxol-5-ylpropionyl-amino)propionate (i.e., fasidotril), their methods of preparation, and novel pharmaceutical compositions containing them. 

The nomenclature used here corresponds to that used in Chemical Abstracts which utilizes the style cyclobuta-, penta-, benzo-, etc., di(heterocycle) if the fused rings are similar. Otherwise the form of heterocycle [cyclopenta-etc.] heterocycle is used. Compound 1 is described as a benzodipyrrole rather than a pyrroloindole, the correct name being benzo[l,2- 5,4- ]dipyrrole. Compound 2 is named as a thieno[3,2- ]benzothiazole and compound 3 is named as a furo[3, 2 ]cyclopenta[l,2-i/l-l,3-dioxole. 

Benzo[l,3]dioxol-5-yl-ethyl)-quinoline (20.0mg 0.072 mmol), BINOL-phosphate 1 (0.5 mg, Imol %), Hantzsch dihydropyridine (43.8 mg,... 

Unexpected reactions occur when benzo[c]furans are treated with o-quinones. Tedder and co-workers reacted 5,6-dimethyl-l,3-diphenyl-benzo[c]furan (210) with o-benzoquinone (211, X = H) and o-chloranil (211, X = Cl) to give dioxoles (212). Subsequent investigations have shown that [714 + 7i4]-cycloadducts (213) are also formed other benzo[t]furans... 

As described in Section IV,C, benzo[c]furans react with o-quinones to give [4 + 4]-adducts and/or dioxoles. The same products are obtained when higher o-quinones such as 9,10-phenanthrenequinone (263), bcn/o[A]-quinoline-5,6-dione (264) and 5,6-chrysenequinone (265) are irradiated with benzo[c]furans (Scheme 17) % the dioxoles may react with a further molecule of excited 263 to give 2 1 adducts (273). 

Compound 299 has also been used as a trapping agent. o-Quinones react with 299 in the same manner as benzo[c]furans (Section 1V,C)" it is noteworthy that 9,10-phenanthrenequinone gives a [4-1- 4]-adduct and a dioxole under thermal conditions (unlike benzo[c]furans). ... 

If we reverse the carbonyl and either the ether or amine groups above, we convert the putatively antiaromatic eight-7t phthalic anhydride and phthalimide into the putatively aromatic ten-7t phenylene carbonate (X = Z = O, Y = CO) (XX) and 2-benzimidazolinone (X = Z = NH, Y = CO) (XXI), and interpolating these last species 2-benzoxazolinone (X = O, Y = CO, Z = NH) (XXII). Calorimetric data are absent for phenylene carbonate (benzo-l,3-dioxole-2-one). 

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