4-hydroxyphenyl dimethyl sulfoxide

Aluminium chloride, Nitrobenzene, 0062 Ammonium hydrogen sulfite, 4545 Benzyltriethylammonium permanganate, 3617 Bis(4-hydroxyphenyl) sulfone, 3497 2-Chloro-5-nitrobenzenesulfonic acid, 2144 1,3 -Dichloro-5,5-dimethyl-2,4-imidazolidindione, 1865 f Dimethyl sulfoxide, 0921... 

For example, treatment of l-(2-hydroxyphenyl)-3-arylpropenones 9 with o-PDA 1 carried out in dimethyl sulfoxide in the presence of sodium acetate under microwave irradiation produces dihydrodiazepines 10 in good yields [10] (Scheme 4.3). Chalcone analogues of dihydroacetic acid 11, as well, containing an 6>r /z0-hydroxyl group, react with 0-PDA in boiling ethanol to produce dihydrobenzodiazepines 12 [11, 12]. 

To a stirred solution of 2,4-dihydro-4- 4-[4-(4-hydroxyphenyl)-l-piperazinyl] phenyl -2-(l-methylpropyl)-3H-l,2,4-triazol-3-one in 100 parts of dimethyl sulfoxide are added 0.3 parts of sodium hydride dispersion 78% and the whole is stirred at 50°C till foaming has ceased. Then there are added 3.7 parts of cis-[2-(2,4-dichlorophenyl)-2-(lH-l,2,4-triazol-l-ylmethyl)-l,3-dioxolan-4-ylmethyl]methanesulfonate and stirring is continued for 3 hours at 100°C. The reaction mixture is cooled and poured onto water. The product is extracted with dichloromethane. The extracts are washed with a diluted sodium hydroxide solution and filtered. The residue is crystallized from 1-butanol. The product yield 4.3 parts (75%) of cis-4- 4-[4- 4-[2-(2,4-dichlorophenyl)-2-(lH-l,2,4-triazol-l-ylmethyl)-l,3-dioxolan-4-ylmethoxy] phenyl -l-piperazinyl]phenyl -2,4-dihydro-2-(methylpropyl)-3H-l,2,4-triazol-3-one. 

The simplest type of template directed cyclization is metal cation induced macrocycliza-tion, as discussed in Section 1.1. Mandolin and co-workers [37] have made a detailed study of the influence of alkali and alkaline earth metal cations on the cyclization of 2-hydroxyphenyl-3,6,9,12-tetraoxa-14-bromotetradecyl ether 28 in methanol and in dimethyl sulfoxide (Scheme 1-8). They studied different sizes of macrocycle and metal cation to determine the most effective combination for cyclization the results from this study will be summarized in Section 1.4.2.3. 

---