Catalyst-free four-component domino synthetic approach toward versatile multicyclic spirooxindole pyran scaffolds
| Autor: | Mohammad Bayat, Aref Mohammadi, Shima Nasri |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
Barbituric acid
Pyrimidine General Chemical Engineering Isatin Pyrazolone 02 engineering and technology General Chemistry 010402 general chemistry 021001 nanoscience & nanotechnology 01 natural sciences Combinatorial chemistry 0104 chemical sciences Catalysis chemistry.chemical_compound Benzylamine chemistry Pyran medicine Methylene 0210 nano-technology medicine.drug |
| Zdroj: | RSC Advances. 9:16525-16533 |
| ISSN: | 2046-2069 |
| DOI: | 10.1039/c9ra03214b |
| Popis: | A new versatile strategy involving a sequential four-component reaction of the nitroketene dithioacetals, alkylamine/benzylamine, isatin and various enolizable active methylene structures (pyrazolone, barbituric acid, 1,3-indandione and 2-hydroxy-1,4-naphthoquinone) as precursors under mild and catalyst-free conditions results in the synthesis of new functionalized spirooxindole pyrans named spiro[indoline-3,4′-pyrano[2,3-c]pyrazol], spiro[indoline-3,5′-pyrano[2,3-d]pyrimidine], spiro[indeno[1,2-b]pyran-4,3′-indoline] and spiro[benzo[g]chromene-4,3′-indoline] in moderate to good yields. The use of various active methylene compounds affords a range of skeletally distinct spirooxindole-based heterocycles with potential biological properties. The present strategy has many advantages, such as convenient one-pot operation, simple workup procedures and straightforward isolation without using tedious purification steps such as column chromatography, progress under catalyst-free condition and high molecular diversity. |
| Databáze: | OpenAIRE |
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