Aroylphenylacetylenes (I) reacted with ethyl and phenyl hydrazinecarboxylates (II) to give ω‐aroylacetophenone‐N‐ethoxycarbonyl‐(Vla‐f) and N‐phenoxycarbonyl‐(VIg‐l) hydrazones, respectively. When these were healed with acetic anhydride they were converted to 5‐aryl‐1‐ethoxycarbonyl‐and 1‐phenoxycarbonyl‐3‐phenylpyrazoles (VII), respectively, which on hydrolysis with rnethanolic potassium hydroxide gave the corresponding 5(3)aryl‐3(5)phenylpyrazoles (VIII).
Reaction of the above acetylenic ketones with guanidine hydrochloride in the presence of sodium carbonate gave the corresponding 2‐amino‐6‐aryl‐4‐phenylpyrimidines (XII). Similarly, reaction of benzoylphenylacetylene with thiourea and with urea in the presence of sodium ethoxide gave rise to 2,4‐diphenylpyrimidine‐2‐thione (XVIII) and 2,4‐diphenyl‐2(1H)pyrimidin‐one (XV), respectively.
135Aryl aldehydes I reacted with a-tetralone to give the corresponding 2-arylidene-1-tetralone 11. Condensation of the latter chalcones with hydrazine, methylhydrazine and phenylhydrazine produced the corresponding benzoklindazoles 111, V and VI respectively. Acetylation of the PH-benzk]indazole derivatives 111 gave the corresponding 2-acetylated compounds IV. The structure of all products was elucidated by chemical and spectroscopic methods.
The condensation of pyrrolyl‐2‐aldehyde or 1‐methyl‐pyrrolyl‐2‐aldehyde with dimethyl succinate, using sodium hydride as condensing agent, gave predominantly the halfesters 1a and 1c respectively. Their structure and (E)‐configuration
were confirmed by their cyclisation to the corresponding indole derivatives 2a–h.
Aryl aldehydes I reacted with 1‐benzosuberone to yield the corresponding 2‐arylidene‐1‐benzosuberones II. Condensation of II with hydrazine and its derivatives provided the substituted 2,3,3a,4,5,6‐hexahydro‐benzo[6,7]cyclohepta[1,2‐c]pyrazoles III‐VI respectively. The structures of all products were assigned by chemical and spectroscopic methods.
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