A new synthesis of bicyclic N,O- and N,S-enaminals by the anionic cyclization of alk-4-ynals with amino alcohols and amino thiols

被引：0
作者：
V. D. Gvozdev
K. N. Shavrin
O. M. Nefedov
机构：
[1] Russian Academy of Sciences,N. D. Zelinsky Institute of Organic Chemistry
来源：
Russian Chemical Bulletin | 2014年 / 63卷
关键词：
alk-4-ynals; aminoalkanols; 2-aminoethanethiol; hexahydro-2; -pyrrolo[2,1-; ]-[1,3]oxazines; hexahydropyrrolo[2,1-; ]oxazoles; hexahydropyrrolo[2,1-; ]thiazoles; 1,3-oxazinanes; hydroamination; anionic cyclization; dimethyl sulfoxide; potassium hydroxide;
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摘要：
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-exodig-cyclization catalyzed by the superbasic system DMSO-KOH.
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页码：409 / 415
页数：6
相关论文
共 68 条
[1]  
Shavrin K N(2008)undefined Mendeleev Commun. 18 300-undefined
[2]  
Gvozdev V D(2010)undefined Russ. Chem. Bull. (Int. Ed.) 59 1451-undefined
[3]  
Nefedov O M(2013)undefined Mendeleev Commun. 23 140-undefined
[4]  
Shavrin K N(2013)undefined Russ. Chem. Bull. (Int. Ed.) 62 2430-undefined
[5]  
Gvozdev V D(1987)undefined Tetrahedron 43 5663-undefined
[6]  
Nefedov O M(1996)undefined Helv. Chim. Acta 79 1026-undefined
[7]  
Shavrin K N(1989)undefined J. Am. Chem. Soc 111 1905-undefined
[8]  
Gvozdev V D(2008)undefined J. Org. Chem 73 6466-undefined
[9]  
Nefedov O M(2004)undefined J. Org. Chem. 69 2888-undefined
[10]  
Gvozdev V D(1991)undefined Eur. J. Med. Chem. 26 85-undefined
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