Sindelar, Karel; Jilek, Jiri O.; Pomykacek, Josef; Sedivy, Zdenek; Protiva, Miroslav published the artcile< Neurotropic and psychotropic agents. Part CXVIII. Synthesis of 2-acetyl and 3-acetyl derivatives of 8-chloro-10-(4-methylpiperazino)-10,11-dihydrodibenzo[b,f]thiepin; 2-acyl-7-substituted thioxanthenes>, COA of Formula: C7H4BrNO4, the main research area is dibenzothiepin methylpiperazino; neurotropic methylpiperazinodibenzothiepin; psychotropic methylpiperazinodibenzothiepin; bactericide methylpiperazinodibenzothiepin; thioxanthene acyl; phenylthiophenylacetic acid cyclization; piperazinodibenzothiepin.
Reaction of 2-chlorodibenzo[b,f]thiepin with AcCl and AlCl3 proceeded under simultaneous acetylation of the nucleus and HCl addition with contraction of the central ring to give the thioxanthene I (R = Cl). Substitution reaction of I (R = Cl) with 1-methylpiperazine gave I (R = 4-methylpiperazino) and the elimination product II (X = CH2) was oxidized by air to II (X = O), also obtained by cyclization of 2-(4-acetylphenylthio)-5-chlorobenzoic acid. Total synthesis of the dibenzothiepins III (R1 = 2-, 3-MeCO; R2 = 4-methylpiperazino) were carried out. They started from the isomeric 2-(4-chlorophenylthio)-5(or4)-nitrobenzoic acids, the first of which was transformed in 6 steps to 5-amino-2-(4-chlorophenylthio)phenylacetic acid, which was cyclized to 2-amino-8-chlorodibenzo[b,f]thiepin-10(11H)-one. The 4-nitro acid, produced in 3 steps the homologous nitro acid, cyclized to 8-chloro-3-nitrodibenzo[b,f]thiepin-10(11H)-one. The Ac groups was introduced in III (R1 = 2-, 3-NH2; R2 = HO) by reaction of the diazonium salts with AcH semicarbazone followed by hydrolysis. The 2-acetyl- and 3-acetyl-8-chloro-10,11-dihydrodibenzo[b,f]thiepin-10-ol yielded by treatment with HCl 2-acetyl- and 3-acetyl-8,10-dichloro-10,11-dihydrodibenzo[b,f]thiepin, isomeric with I (R = Cl). Substitution reactions with 1-methylpiperazine gave III (R1 = 2-, 3-MeCO, R2 = 4-methylpiperazino) together with products of elimination, i.e. 2-acetyl- and 3-acetyl-8-chlorodibenzo[b,f]thiepin I (R = 4-methylpiperazino) when administered i.v. to mice, had a high central depressant activity, III (R1 = 2-MeCO, R2 = 4-methylpiperazino) had only mild activity; both substances in the test on rats were practically devoid of cataleptic activity (LD50 and ED50 given).
Collection of Czechoslovak Chemical Communications published new progress about Cyclocondensation reaction, intramolecular. 16426-64-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrNO4, COA of Formula: C7H4BrNO4.
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary