11H-dibenzo[b,e]azepines. Part 1. Synthesis and ir spectra of dibenzo[b,f][1,4]oxazepines

11H-dibenz[b,e]azepines. Part 4. Protonated and N-alkylated compounds of dibenz[b,f]-1,4-ox(thia)azepine

“…The initial ox(thia)azepines were synthesized as described elsewhere [4] (XII). A solution of 4.8 g of compound Xa in 30 ml of water was kept for 3 h at room temperature, alkalized with aqueous ammonia to pH 9 -10, and extracted with ether.…”

“…A comparison of the IR spectra of the products to those of the initial bases I showed a significant difference only in the region of 1610-1660 cm-k In all cases, the passage from base to salt leads to disappearance of the band at 1610-1625 cm-i (corresponding to the stretching vibrations of imino groups [4]) and the appearance of a new band shifted by 20-40 cm-l toward higher frequencies (1640 -1660 cm-i). According to the data obtained for some other imino compounds [5,6], the new band should be assigned to the stretching vibrations of C=N + groups.…”

“…In continuation of our investigations devoted to the synthesis of new effective antidepressants [3,4], we have synthesized a series of previously unreported salts of dibenz[b,f]-1,4-ox(thia)azepine and characterized them with respect to optical and some other properties.…”

Dibenz[b,e]azepines. Part 3. Acid hydrolysis

“…Dibenz[b,e]azepines were synthesized as described elsewhere [2], by cyclization of the corresponding amides at I20-130~ in a polyphosphoric acid solution.…”

“…For this reason, in continuation of our previous work [1,2] on the synthesis of effective antidepressants in the series of dibenz[b,e]azepines, we have studied their behavior in aqueous acid solutions.For this purpose, we have used the method of Raman scattering providing identification of the hydrolysis products immediately in the reaction mixture.A comparison of the Raman spectra of a crystalline sample of dibenz [b,f] [1,4]oxazepine Ia (this compound is virtually insoluble in water) and its aqueous hydrochloric acid (10%) solution reveals a most pronounced difference in the region of 1600 -1700 cm-I. For example, a band at 1613 cm-I (vC=N) characteristic of the Raman spectrum of solid Ia is absent in the spectrum of the solution, but the latter spectrum displays a new band at 1658 cm-I, which is typical of the aqueous solutions of aromatic aldehydes [3].…”