3,3-Dimethoxypropylsulfonyl Group: A new versatile protecting and activating group for amine synthesis
| Autor: | Takeshi Nishii, Yuki Takeuchi, Hiroto Kaku, Yuta Kawada, Mitsuyo Horikawa, Izumi Sakamoto, Takanori Naito, Kazuyoshi Makida, Tetsuto Tsunoda, Kazuya Iwaoka |
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| Rok vydání: | 2018 |
| Předmět: |
Aqueous solution
Primary (chemistry) biology 010405 organic chemistry Chemistry Organic Chemistry Alkylation 010402 general chemistry biology.organism_classification 01 natural sciences Biochemistry Chloride 0104 chemical sciences Ammonia chemistry.chemical_compound Group (periodic table) Drug Discovery medicine Organic chemistry Amine synthesis Epilachna varivestis medicine.drug |
| Zdroj: | Tetrahedron. 74:3052-3060 |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/j.tet.2018.04.088 |
| Popis: | 3,3-Dimethoxypropylsulfonyl (Dimps) chloride was prepared and used as a new versatile sulfonating agent for ammonia, primary and secondary amines to afford corresponding Dimps-amides in excellent yields. The resulting N-nonsubstituted and N-monosubstituted Dimps-amides, activated amines, were alkylated satisfactorily under new Mitsunobu conditions. The Dimps group was removed by treatment in aqueous solution under acidic followed by basic conditions. Furthermore, epilachnene, the defensive droplets from the Mexican bean beetle, Epilachna varivestis, was synthesized utilizing this Dimps methodology in short steps. |
| Databáze: | OpenAIRE |
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