4-(Trihydro-2H-1,2-thiazole-

No abstract

4-thiadiazolylsteroids were synthesized from the appropriate hydrazonoyl halides and alkyl carbodithioates containing steroid moiety. The newlysynthesized compounds were elucidated by elemental analysis, spectral data, and alternative synthetic route whenever possible.

SummaryArylnaphthyl ketones condense with diethyl succinate yielding the stereoisomeric half-esters 2a-2d which were subjected to a series of reactions leading to 1-phenylphenanthrene and 1,l'-binaphthyl derivatives. (E)-3-Ethoxycarbonyl-4-(4-methoxynaphth-l-yl)-4-arylbut-3-enoic acids (2b-d) were converted finally into the corresponding naphtho [ 1,2-c]fluorenones (9). The structure of the products was established by IR. and UV. spectroscopy. The effect of substituents on the relative proportions of (E)-and (Z)-half-esters 2 was determined by chromatography and UV. spectroscopy. Awad et al.[ 13 claimed that the condensation of 1-benzoylnaphthalene (1 a) with diethyl succinate in the presence of potassium t-bitoxide in t-butyl alcohol produced ( E ) half-ester 2a as the sole product. This result was attributed either to steric or/and polar factors. We have now found that the (Z)-2a isomer is also produced.In order to study the r6le of the above mentioned factors in determining the ratio of the isomeric half-esters produced in this Stobbe condensation, aryl naphthyl ketones containing substituents of different polar nature either in the naphthyl or in both the naphthyl and the phenyl groups, 1 -benzoyl-4-methoxynaphthalene (1 b), l-(p-methoxybenzoyl)-4-methoxynaphthalene (1 c) and 1-@-chlorobenzoy1)-4-methoxynaphthalene (Id), besides 1-benzoylnaphthalene (1 ai) were condensed with diethyl succinate.The new ketones l c and I d were prepared by Friedel-Crajts condensation of p-methoxybenzoyl and p-chlorobenzoyl chloride with 1 -methoxynaphthalene [2].I -Benzoylnaphthalene (1 a) and diethyl succinate. After condensation of 1-benzoylnaphthalene (1 a) with diethyl succinate [ 11, the crude half-ester mixture 2a (53%) was directly cyclized with sodium acetate in acetic anhydride. After crystallization the neutral product gave 1-acetoxy-3-ethoxycarbonyl-4-phenylphenanthrene (3a) (84%). Chromatography of the residue gave 4-acetoxy-2-ethoxycarbonyl-1,l'-binaphthyl (4a) (13%). The same relative amounts of 3a and 4a were estimated by the application of Dewar & Urch spectrophotometric method [3].

Several new aminopyrazolo [ l,S-u]pyrimidines were synthesised by condensation of 33-diami-no4-(ethoxycarbonyl)pyrazoIe (1) with b-bifunctional reagents. The azo analogues of pyrazolo [l,5-u]pyrimidines, i. e. pyrazolo[l,4-c]-ar-triazines, were synthesised by coupling of diazotized 1 with agents containing active hydrogen. Reaktionen mit heteroqLliscaen Amidinen, ll. M i t t . : Syntheae e w e r nener Aminopyrrzolo[l,S-n]pyrhnicUn-Derivate und 2 -A m i n o [ l , S -c ] -~-t eEinige neue Aminopyrazolo[ 1,5-a]pyrimidin-Derivate wurden durch Umsetzung von 3,5-Diami- no-4-ethoxycarbonyl-pyrazol(l) mit p-bifunktionellen Reagenzien synthetisiert . Die Azoanalogen Pyrazolo[l,S-c]-as-tri~ne wurden durch Umsetzung von diazotiertem 1 mit Reagenzien mit aktivem Wasserstoff hergestellt.Schistosomiasis is considered to be one of the most difficult diseases to treat"). Accordingly considerable attention has been directed toward development of chemotherapeutic agents. Recently Sengu at a l ' ) have reported that certain pyrazolo[ 1 ,5-u]pyrimidines have considerable antischistosomal activity. 0365-6233/lWM84713 S U2.50/0 0 Verlae Chemie GmbH, Weinheim 1983 714 Kandeel, Baghos, Mohareb and ElnagdiArch. Pharm.