Synthesis of N ‐Alkyl and N‐H ‐Carbazoles through S N Ar‐Based Aminations of Dibenzothiophene Dioxides

Autor:	Hideki Yorimitsu, Keisuke Nogi, Atsushi Kaga
Rok vydání:	2019
Předmět:	chemistry.chemical_classification Base (chemistry) 010405 organic chemistry Organic Chemistry Intermolecular force Intramolecular cyclization General Chemistry 010402 general chemistry Alkali metal 01 natural sciences Medicinal chemistry Catalysis 0104 chemical sciences chemistry.chemical_compound chemistry Nucleophilic aromatic substitution Dibenzothiophene Alkyl Amination
Zdroj:	Chemistry – A European Journal. 25:14780-14784
ISSN:	1521-3765 0947-6539
DOI:	10.1002/chem.201903916
Popis:	Alkyl amines have become available for the synthesis of diverse N-alkyl carbazoles through twofold SN Ar aminations of dibenzothiophene dioxides by using alkali metal bases. Of particular importance is the choice of counter cations on alkali metal bases, that is, i) the use of Li base for the efficient intermolecular reaction and ii) the sequential addition of heavier alkali metal bases (Na, K, or Cs) to promote intramolecular cyclization in a one-pot manner. This protocol also enables the cascade synthesis of N-H-carbazoles by using 2-phenylethylamine by removal of the 2-phenethyl group from N-(2-phenethyl) carbazoles in a single operation.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::c77b9e1385515d239f257dc6dc92bf9b https://doi.org/10.1002/chem.201903916 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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