Journal
RUSSIAN CHEMICAL BULLETIN
Volume 62, Issue 11, Pages 2430-2437Publisher
SPRINGER
DOI: 10.1007/s11172-013-0351-3
Keywords
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
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Funding
- 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]
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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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