Abstract

The condensation of 3-benzyl-2-sulfanylidene-2,3-dihydro-1H-spiro[benzo[h]quinazoline-5,1′-cyclo­heptan]-4(6H)-one with 5,5-dialkyl-2-(chloromethyl)benzo[h]quinazolines gave bis-benzo[h]quinazoline compounds in which the spiro[benzo[h]quinazoline-5,1′-cycloheptane] fragment is linked through the 2-position to another benzo[h]quinazoline moiety via a SCH₂ spacer. 3-Benzyl-2-sulfanylidene-2,3-dihydro-1H-spiro­[benzo[h]quinazoline-5,1′-cycloheptan]-4(6H)-one reacted under similar conditions with methylene iodide to produce 2,2′-[methylenebis(sulfanediyl)]bis{3-benzyl-3H-spiro[benzo[h]quinazoline-5,1′-cycloheptan]-4(6H)-one}. The initial benzo[h]quinazoline was converted to 2-hydrazinyl derivative which underwent elimination of the hydrazine moiety by the action of alkali with the formation of 3-benzyl-3H-spiro[benzo[h]quinazoline-5,1′-cycloheptan]-4(6H)-one. The 2-hydrazinyl derivative was used to obtain the corresponding phenylhydrazone, thiosemicarbazide, and 4-benzyl-4H-spiro[benzo[h][1,2,4]triazolo[4,3-a]quinazoline-6,1′-cycloheptanone]-5(7H)-one. The alkylation of 4-benzyl-1-sulfanyl-4H-spiro[benzo[h][1,2,4]triazolo[4,3-a]quinazoline-6,1′-cycloheptan]-5(7H)-one with alkyl halides afforded the corresponding 1-alkylsulfanyl derivatives. The synthe­sized compounds were tested for antibacterial activity.

中文翻译：

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新型3-苄基螺[苯并[h]喹唑啉-5,1'-环庚烷]-4(6H)-酮衍生物的合成及抗菌活性

 抽象的

3-苄基-2-硫亚基-2,3-二氢-1H-螺[苯并[h]喹唑啉-5,1'-环庚烷]-4(6H)-酮与5,5-二烷基-2-的缩合(氯甲基)苯并[h]喹唑啉得到双苯并[h]喹唑啉化合物，其中螺环[苯并[h]喹唑啉-5,1'-环庚烷]片段通过2位连接到另一个苯并[h]喹唑啉通过 SCH ₂ 间隔基的部分。 3-苄基-2-硫亚基-2,3-二氢-1H-螺[苯并[h]喹唑啉-5,1'-环庚烷]-4(6H)-酮在类似条件下与二碘甲烷反应生成2,2 '-[亚甲基双(硫烷二基)]双{3-苄基-3H-螺[苯并[h]喹唑啉-5,1'-环庚烷]-4(6H)-酮}。最初的苯并[h]喹唑啉转化为2-肼基衍生物，在碱的作用下消除肼部分，形成3-苄基-3H-螺环[苯并[h]喹唑啉-5,1'-环庚烷]-4(6H)-一。利用2-肼基衍生物得到相应的苯腙、氨基硫脲和4-苄基-4H-螺[苯并[h][1,2,4]三唑并[4,3-a]喹唑啉-6,1'-环庚酮]-5(7H)-一。 4-苄基-1-硫基-4H-螺[苯并[h][1,2,4]三唑并[4,3-a]喹唑啉-6,1'-环庚烷]-5(7H)-酮的烷基化与烷基卤化物反应得到相应的1-烷基硫基衍生物。测试了合成化合物的抗菌活性。