期刊
RUSSIAN CHEMICAL BULLETIN
卷 63, 期 2, 页码 409-415出版社
SPRINGER
DOI: 10.1007/s11172-014-0445-6
关键词
alk-4-ynals; aminoalkanols; 2-aminoethanethiol; hexahydro-2H-pyrrolo[2,1-b]-[1,3]oxazines; hexahydropyrrolo[2,1-b]oxazoles; hexahydropyrrolo[2,1-b]thiazoles; 1,3-ox-azinanes; hydroamination; anionic cyclization; dimethyl sulfoxide; potassium hydroxide
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]
- Presidium of the Russian Academy of Sciences
A reaction of alk-4-ynals with aliphatic amino alcohols or 2-aminoethanethiol in the system DMSO-KOH gives bicyclic N,O- and N,S-enaminals: 6-methylidenehexahydro-2H-pyrrolo[2,1-b][1,3] oxazines, 5-methylidenehexahydropyrrolo[2,1-b] oxazoles, or 5-methyl-idenehexahydropyrrolo[2,1-b] thiazoles. The reaction proceeds through the formation of equilibrium mixtures of the corresponding imines and monocyclic aminals with subsequent 5-exo-dig-cyclization catalyzed by the superbasic system DMSO-KOH.
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