Synthesis and transformations of 6,6,7,7-tetramethyl-2-quinuclidone

Autor:	E. S. Nikitskaya, L. N. Yakhontov, E. I. Levkoeva
Rok vydání:	1971
Předmět:	chemistry.chemical_compound Nucleophile Chemistry Organic Chemistry Organic chemistry Acid hydrolysis Ether Medicinal chemistry Chemical reaction Phenyllithium Acetone cyanohydrin Methyl iodide Quinuclidine
Zdroj:	Chemistry of Heterocyclic Compounds. 7:349-354
ISSN:	1573-8353 0009-3122
DOI:	10.1007/bf00944421
Popis:	6,6,7,7-Tetramethyl-2-quinuclidone was synthesized, and its differences from the usual amides were shown. It enters into three types of chemical reactions: 1) the N-CO bond is broken under the influence of protic nucleophilic agents (water, alcohols, amines, hydroxylamine, and hydrazines), and nucleophilic agents are acylated by the (2,2,6,6-tetramethyl-4-piperidyl)-acetic acid residue; 2) the N-C(CH3)2 bond is broken by reaction with nucleophilic agents in aprotic media (phenyllithium in ether, PCl5 in benzene, acetone cyanohydrin, and LiAlH4 in ether) to form 4-substituted 6,6-dimethyl-2-piperidones; 3) reactions with the preservation of the quinuclidine ring occur on treatment with electrophilic reagents (hydrogen chloride and methyl iodide) in aprotic solvents and during reduction.
Databáze:	OpenAIRE
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