Reduction of imidazolium salts – An approach to diazocines and diazocanes
| Autor: | Kostiantyn Nazarenko, Kostiantyn Shvydenko, Aleksandr N. Kostyuk, Tetiana Shvydenko, Oleksii V. Gutov, Sergey Yu. Boron, Andrey A. Tolmachev |
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| Rok vydání: | 2017 |
| Předmět: |
010405 organic chemistry
Chemistry Organic Chemistry 010402 general chemistry Cleavage (embryo) 01 natural sciences Biochemistry Medicinal chemistry 0104 chemical sciences Acetic acid chemistry.chemical_compound Sodium triacetoxyborohydride Sodium borohydride Nucleophile Drug Discovery Organic chemistry |
| Zdroj: | Tetrahedron. 73:6942-6953 |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/j.tet.2017.10.053 |
| Popis: | A convenient approach to diazocine derivatives 8,9 starting from 1,2-polymethyle-neimidazolium salts 4 was developed. The polymethylenimidazolium salts 4 are partially reduced with sodium borohydride in DMF to give 5,6,7,7a-tetrahydro-1H-pyrrolo[1,2- a ]imidazoles 5 or under more forcing conditions – (sodium triacetoxyborohydride in acetic acid) with cleavage of the endocyclic C N bond affording diamines 6 . Tertiary salts 7 readily prepared from compounds 5 react with NaBH 4 and KCN nucleophiles with cleavage of the endocyclic N C bond to form diazocine derivatives 8,9 . |
| Databáze: | OpenAIRE |
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