期刊
RUSSIAN CHEMICAL BULLETIN
卷 62, 期 11, 页码 2430-2437出版社
SPRINGER
DOI: 10.1007/s11172-013-0351-3
关键词
alk-4-ynals; 1,2-diaminoethane; 1,3-diaminopropanes; hexahydropyrrolo[1,2-a]-imidazoles; octahydropyrrolo[1,2-a]pyrimidines; hexahydropyrimidines; imidazolidines; hydroamination; cascade cyclization; dimethyl sulfoxide
资金
- Council on Grants at the President of the Russian Federation (Program of State Support for Leading Scientific Schools of the Russian Federation) [NSh_604.2012.3]
- Russian Academy of Sciences [OKh-01]
A cyclization of alk-4-ynals with aliphatic diamines in DMSO upon treatment with KOH was found to lead to bicyclic N,N-enaminals. The studies of this reaction showed that 1,3-di-aminopropane and N-methyl-1,3-diaminopropane gave (E)-6-(arylmethylidene) octahydro-pyrrolo[1,2-a] pyrimidines in 45-78% yields, whereas 1,2-diaminoethane gave 5-(aryl-methylidene) hexahydropyrrolo[1,2-a] imidazoles as mixtures of E-and Z-isomers in up to 75% total yield. The mechanism of these new cascade cyclization reactions includes formation of the equilibrium mixtures of imines and cyclic aminals with subsequent intramolecular hydroamination of the triple bond having considerable ionic character.
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