含1,4-苯二氧环磺酰基的新型取代1,5-苯并噻唑类化合物的合成

Sandhya Chhakra, A. Mukherjee, Harlal Singh, S. Chauhan
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引用次数: 0

摘要

描述了一种含磺酰基的新型2,3,4-三取代1,5-苯并噻唑类药物(4a-e)的有效合成。以3-(1,4-二氧氧烷-6-磺酰基)-2,4-二甲基/4-甲基-2-苯基/2,4-二苯基/2-乙氧基-4-甲基/2,4-二氧基丙烷-1,3-二酮(3ae)与2-氨基苯硫醇和znonanooparticles /吡啶为原料合成了化合物(4a-e)。化合物(3a-e)由1,4-二氧环-6-磺酰氯(1)与2,4-二甲基/4-甲基-2-苯基/2,4-二苯基/2-乙氧基-4-甲基/2,4-二氧基丙烷-1,3-二酮(2a-e)反应生成。用柱层析法(苯:CHCl3, 40:60, 30:70, 20:80, 10:90)纯化得到苯并噻唑类化合物(4a-e),甲醇结晶。以(CHCl3: CH3OH, 9:1)为流动相,采用薄层色谱法检测化合物的纯度。通过元素分析、红外光谱、核磁共振氢谱、核磁共振13C谱和质谱分析确定了化合物的结构。本文对标题化合物在基态下的前沿分子轨道进行了推测性研究。用柔软度、亲电性、电负性、HOMO-LUMO能隙等不同描述符计算了分子的反应性。
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Synthesis of Novel Substituted 1,5-Benzothiazepines Containing 1,4-Benzodioxane Sulfonyl Moiety
An efficient synthesis of novel 2,3,4-trisubstituted 1,5-benzothiazepines (4a-e) incorporating the sulfonyl group is described. Compound (4a-e) was synthesized by the reaction of 3-(1,4-dioxane-6-sulfonyl)-2,4-dimethyl/4-methyl-2-phenyl/2,4-diphenyl/2-ethoxy-4-methyl/2,4-diethoxy propane-1,3-dione (3ae) with 2-aminobenzenethiol with ZnOnanoparticles/pyridine. Formation of compound (3a-e) was achieved by the reaction of 1,4-dioxane-6-sulfonyl chloride (1) with 2,4-dimethyl/4-methyl-2-phenyl/2,4-diphenyl/2-ethoxy-4-methyl/2,4-diethoxy propane-1,3-dione (2a-e). The benzothiazepines (4a-e) obtained were purified by column chromatography (benzene: CHCl3, 40:60, 30:70, 20:80, 10:90) and crystallized from methanol. The purity of the compounds was checked by TLC using (CHCl3: CH3OH, 9:1) as the mobile phase. The structure of the compounds has been established by elemental, IR, 1H NMR, 13C NMR and Mass spectral analyses. Frontier molecular orbitals of the title compounds have been studied in the ground state speculatively. The reactivity of a molecule using diverse descriptors such as softness, electrophilicity, electronegativity, HOMO-LUMO energy gap is calculated additionally discussed.
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