دورية أكاديمية
Using Sodium Hydride and Potassium Carbonate as Bases in Synthesis of Substituted 2-Amino-4-aryl-7-propargyloxy-4H-chromene-3-carbonitriles.
| العنوان: | Using Sodium Hydride and Potassium Carbonate as Bases in Synthesis of Substituted 2-Amino-4-aryl-7-propargyloxy-4H-chromene-3-carbonitriles. |
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| المؤلفون: | Thanh ND; Faculty of Chemistry, VNU University of Science (Vietnam National University, Ha Noi), 19 Le Thanh Tong, Hoan Kiem, Ha Noi, Vietnam., Hai DS; Faculty of Chemistry, VNU University of Science (Vietnam National University, Ha Noi), 19 Le Thanh Tong, Hoan Kiem, Ha Noi, Vietnam., Bich VTN; Faculty of Chemistry, VNU University of Science (Vietnam National University, Ha Noi), 19 Le Thanh Tong, Hoan Kiem, Ha Noi, Vietnam., Hien PTT; Faculty of Chemistry, VNU University of Science (Vietnam National University, Ha Noi), 19 Le Thanh Tong, Hoan Kiem, Ha Noi, Vietnam., Duyen NTK; Faculty of Chemistry, VNU University of Science (Vietnam National University, Ha Noi), 19 Le Thanh Tong, Hoan Kiem, Ha Noi, Vietnam., Mai NT; Faculty of Chemistry, VNU University of Science (Vietnam National University, Ha Noi), 19 Le Thanh Tong, Hoan Kiem, Ha Noi, Vietnam., Dung TT; Faculty of Chemistry, VNU University of Science (Vietnam National University, Ha Noi), 19 Le Thanh Tong, Hoan Kiem, Ha Noi, Vietnam., Van HTK; Faculty of Chemistry, VNU University of Science (Vietnam National University, Ha Noi), 19 Le Thanh Tong, Hoan Kiem, Ha Noi, Vietnam., Toan VN; Faculty of Chemistry, VNU University of Science (Vietnam National University, Ha Noi), 19 Le Thanh Tong, Hoan Kiem, Ha Noi, Vietnam., Toan DN; Faculty of Chemistry, VNU University of Science (Vietnam National University, Ha Noi), 19 Le Thanh Tong, Hoan Kiem, Ha Noi, Vietnam., Dang LH; Faculty of Chemistry, VNU University of Science (Vietnam National University, Ha Noi), 19 Le Thanh Tong, Hoan Kiem, Ha Noi, Vietnam. |
| المصدر: | Current organic synthesis [Curr Org Synth] 2019; Vol. 16 (3), pp. 423-430. |
| نوع المنشور: | Journal Article; Research Support, Non-U.S. Gov't |
| اللغة: | English |
| بيانات الدورية: | Publisher: Bentham Science Publishers Country of Publication: United Arab Emirates NLM ID: 101208457 Publication Model: Print Cited Medium: Internet ISSN: 1570-1794 (Print) Linking ISSN: 15701794 NLM ISO Abbreviation: Curr Org Synth Subsets: PubMed not MEDLINE; MEDLINE |
| أسماء مطبوعة: | Original Publication: Saif Zone, Sharjah, U.A.E. ; San Francisco, CA : Bentham Science Publishers, c2004- |
| مستخلص: | Aims and Objective: 1-Alkynes are the important precursors for the CuAAC click chemistry. The hybrid of 1,2,3-triazole ring to the chromene ring and sugar moiety could bring some remarkable biological properties. Propargyl derivatives are usually used in the click chemistry. This article reported the synthesis of 2-amino-4-aryl-7-propargyloxy-4-aryl-4H-chromene-3-carbonitriles using propargyl bromide as alkylation agent and the use of potassium carbonate and sodium hydride as bases in the conversion of 2-amino-4-aryl-7- hydroxy-4-aryl-4H-chromene-3-carbonitriles into corresponding propargyl ethers in Williamson's ether synthesis. Materials and Methods: The use of CTAB for the synthesis of benzylidene malononitriles and anhydrous potassium carbonate as a catalyst in absolute ethanol in the synthesis of 2-amino-7-hydroxy-4H-chromene-3- carbonitriles is an efficient and simple synthetic method. Propargyl ether compounds of these 4H-chromene-3- carbonitriles were obtained from the alkylation reaction by propargyl bromide. Two procedures were applied: K2CO3 as a base in acetone solvent (Procedure A) and NaH as a base in DMF solvent (Procedure B). The single-crystal X-ray structure of propargyl ether 5e has been studied. Results: The use of K2CO3 and NaH as bases in the Williamson's ether synthesis from 2-amino-7-hydroxy-4Hchromene- 3-carbonitriles showed that Procedure B was the better route and gave ethers in the higher yields. 2- Amino-4-aryl-7-propargyloxy-4-aryl-4H-chromene-3-carbonitriles were obtained from corresponding 7- hydroxy-4H-chromene-3-carbonitriles. Yields of ethers 5a-i were 70-89% and 80-96%, respectively depending on the used procedures. Conclusion: The described methods are simple, clean and environmentally friendly alternatives for the preparation of 2-amino-4-aryl-7-hydroxy-4H-chromene-3-carbonitriles. The conditions for the transformation of these compounds into propargyl ethers include dried DMF as a solvent, NaH as a base and reaction time of 2 h at the room temperature. A series of 2-amino-4-aryl-7-hydroxy-4-aryl-4H-chromene-3-carbonitriles were obtained based on investigated reaction condition. (Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.net.) |
| فهرسة مساهمة: | Keywords: 4H-Chromene; Williamson’s ether synthesis; multi-component reaction; potassium carbonate; propargyl ether; sodium hydride |
| تواريخ الأحداث: | Date Created: 20200128 Date Completed: 20200413 Latest Revision: 20200413 |
| رمز التحديث: | 20221213 |
| DOI: | 10.2174/1570179416666190104124652 |
| PMID: | 31984904 |
| قاعدة البيانات: | MEDLINE |
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