Moradi Ali Varasteh
Department of Chemistry, Gorgan Branch, Islamic Azad University, Gorgan. Iran.
Comb Chem High Throughput Screen. 2017;20(1):77-81. doi: 10.2174/1386207319666161228154258.
A simple and efficient procedure is achieved for the synthesis of indole-2-one derivatives via three-component reaction of N-alkylisatin, activated acetylenic compounds and alkyl bromide in the presence of triphenylphosphine in water under two conditions; room temperature and microwave irradiation.
All chemicals used in this work were prepared from Fluka (Buchs, Switzerland) and were used without further purification. N-alkylisatin were synthesized in the laboratory in the procedure that is reported in the literature. Electrothermal 9100 apparatus is employed for measuring of melting points of products. Elemental analyses for C, H, and N were performed with Heraeus CHN-O-Rapid analyzer. Mass spectra were recorded on a FINNIGAN-MAT 8430 spectrometer operating at an ionization potential of 70 eV. Measurement of IR spectra was performed by Shimadzu IR-460 spectrometer. 1H, and 13C NMR spectra were evaluated with a BRUKER DRX- 500 AVANCE spectrometer at 500.1 and 125.8 MHz, respectively.
The results were demonstrated that simple mixing of N-alkylisatin, dialkyl acetylenedicarboxylate and alkyl bromides in the presence of triphenylphosphine by using of microwave condition is the efficient method for preparation of indole derivatives in good yields. In the optimized reaction conditions, water is solvent and temperature of the mixture of reaction is 80 oC.
In this study, the reaction of activated acetylenic compounds with N-alkylisatin and alkyl bromide in the presence of triphenylphosphine is investigated which is led to a facile synthesis of some functionalized indoles.
实现了一种简单高效的方法，即在水相中，在三苯基膦存在下，通过N - 烷基异吲哚酮、活性炔属化合物和烷基溴的三组分反应，在室温及微波辐射两种条件下合成吲哚 - 2 - 酮衍生物。
本研究中使用的所有化学试剂均购自瑞士布赫的Fluka公司，无需进一步纯化即可使用。N - 烷基异吲哚酮是按照文献报道的方法在实验室中合成的。使用电热9100仪器测量产物的熔点。用Heraeus CHN - O - Rapid分析仪进行C、H和N的元素分析。在电离电位为70 eV的FINNIGAN - MAT 8430光谱仪上记录质谱。用岛津IR - 460光谱仪测量红外光谱。分别在500.1 MHz和125.8 MHz下，用BRUKER DRX - 500 AVANCE光谱仪对1H和13C NMR光谱进行评估。
结果表明，在微波条件下，在三苯基膦存在下将N - 烷基异吲哚酮、二烷基乙炔二羧酸酯和烷基溴简单混合是高产率制备吲哚衍生物的有效方法。在优化的反应条件下，以水为溶剂，反应混合物的温度为80℃。
本研究考察了在三苯基膦存在下活性炔属化合物与N - 烷基异吲哚酮和烷基溴的反应，该反应可简便地合成一些功能化吲哚。
