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We synthesized 4-(l-adamantyl)phenol (llI) [3] and 4-(l-adamantyl)resorcinol (IV) by refluxing l-bromoadamantane with phenol or resorcinol in benzene until the evolution of hydrogen bromide ceased. We were able to get both the mono and dibromo derivatives by bromination of (III), depending on the reaction conditions. 2,6-Dibromo-4-(l-adamantyl)phenol (V) was formed in 89.3% yield when III was treated with bromine in a mixture of methanol and acetic anhydride. We got the same compound when the reaction was carried out in carbon tetrachloride or glacial acetic acid, though the yield was slightly lower, 83% and 75%, respectively. We used a milder brominating agent, dioxane dibromide in ether, to prepare 2-bromo4-(l-adamantyl)phenol (VI). In regard to the iodo derivatives, 2-iodo-4-(!-adamantyl)phenol (VII) was readily formed by treatment of III with iodine monoch!oride in glacial acetic acid. The yield of VII was 93%. We turned to a stronger iodinating agent, iodine in morpholine, to introduce a second iodine atom, but were unable to get the desired compound, isolating only the monoiodo derivative VII in lower yield, 50%.

We synthesized and studied the antiviral activity of thieno[3,2-b]indole derivatives (I-V). The first derivative of this series, 2-methyl-3-carbethoxythieno[3,2-b]indole (I), was previously obtained by condensation of 2-methyl-3-carbethoxy-4-hydroxythiophene with phenylhydrazine by the Fischer method [7]. We extended the field of application of this reaction and synthesized thieno[3,2-b]indoles (II-V) by the reaction of phenylhydrazine derivatives with 2-methyl-3-carbethoxy-4-hydroxythiophene. The corresponding carboxylic acids (VIX) were obtained from compounds (I-V), and the diethylaminoethyl ester (XI) from (VI). By the action of hydrazine hydrate on compound I, the hydrazide (XII) is formed, which with ptoluenesulfonyl chloride gives tosylhydrazide (XIII), and with ketones, hydrazones (XIV-XVIII). Hydrazides XII-XVIII are interesting since their analogs have antitubercular and antimicrobial activity [8-10]. The structure of the compounds obtained was confirmed by IR spectra. In the IR spectra of I-V, stretching vibration bands of the carbonyl group are observed in the 1670-1690 cm -I region, as well as a band at 3400 cm -I which is characteristic of the NH group and disappears in N-substituted derivatives, and absorption bands in the 790-810 cm -~ region characteristic of the thiophene ring. In the IR spectrum of compound X, the stretching vibration band of the carbonyl group is shifted to 1660 cm -I.