Microwave-assisted synthesis of imidazoles: Reaction of p-toluenesulfonylmethyl isocyanide and polymer-bound imines
| Autor: | Swapan Kumar Samanta, Irene Kylänlahti, Jari Yli-Kauhaluoma |
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| Rok vydání: | 2005 |
| Předmět: |
Trimethyl orthoformate
Polymers Isocyanide Clinical Biochemistry Pharmaceutical Science 010402 general chemistry 01 natural sciences Biochemistry Chemical synthesis Tosyl Compounds chemistry.chemical_compound Nitriles Drug Discovery Polymer chemistry Trifluoroacetic acid Organic chemistry Orthoester Microwaves Molecular Biology Molecular Structure 010405 organic chemistry Organic Chemistry TosMIC Imidazoles Cycloaddition 0104 chemical sciences chemistry Cyclization 1 3-Dipolar cycloaddition Molecular Medicine Imines |
| Zdroj: | Bioorganic & Medicinal Chemistry Letters. 15:3717-3719 |
| ISSN: | 0960-894X |
| DOI: | 10.1016/j.bmcl.2005.05.066 |
| Popis: | A convenient method for the synthesis of 1,5-disubstituted imidazoles has been developed on a polymeric support using base-promoted 1,3-dipolar cycloaddition reaction of p-toluenesulfonylmethyl isocyanide (TOSMIC) with immobilized imines under microwave irradiation. The immobilized imines were synthesized by the reaction of various primary benzyl amines with 4-formyl-3-methoxyphenoxymethyl polystyrene in the presence of trimethyl orthoformate at room temperature. Cleavage from the polymeric support using trifluoroacetic acid gave the desired 1,5-disubstituted imidazoles with excellent yield and high purity. |
| Databáze: | OpenAIRE |
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