Dual Behavior of Isatin-Based Cyclic Ketimines with Dicarbomethoxy Carbene: Expedient Synthesis of Highly Functionalized Spirooxindolyl Oxazolidines and Pyrrolines
| Autor: | Tamilselvan Rajasekaran, B. V. Subba Reddy, Govindaraju Karthik, B. Sridhar |
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| Rok vydání: | 2013 |
| Předmět: |
Isatin
Thiosemicarbazones Indoles Azomethine ylide Stereoisomerism Crystallography X-Ray Biochemistry chemistry.chemical_compound Nitriles Organic chemistry Molecule Pyrroles Spiro Compounds Physical and Theoretical Chemistry Oxazoles Dimethyl acetylenedicarboxylate Cycloaddition Reaction Molecular Structure Organic Chemistry Cycloaddition chemistry Imines Azo Compounds Carbene |
| Zdroj: | Organic Letters. 15:1512-1515 |
| ISSN: | 1523-7052 1523-7060 |
| Popis: | A highly stereo-, regio-, and chemoselective method has been devised for the synthesis of a wide range of spirooxindolyl oxazolidines via an intermolecular 1,3-dipolar cycloaddition of carbonyl ylides generated from dimethyl diazomalonate and aromatic aldehydes, with cyclic ketimines using 5 mol % of Rh2(OAc)4 under mild conditions. Similarly, highly functionalized spirooxindolyl pyrrolines have also been prepared through 1,3-dipolar cycloaddition of azomethine ylides generated from dimethyl diazomalonate and cyclic ketimines, with dimethyl acetylenedicarboxylate. |
| Databáze: | OpenAIRE |
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