First example of a 1,3-dipolar cycloaddition of 1,3-thiazole-5(4H)-thiones with an azomethine ylide; Crystal structures of a pair of stereoisomeric adducts

被引：0
作者：
Mloston, G [1 ]
Linden, A [1 ]
Heimgartner, H [1 ]
机构：
[1] UNIV ZURICH,INST ORGAN CHEM,CH-8057 ZURICH,SWITZERLAND
来源：
POLISH JOURNAL OF CHEMISTRY | 1997年 / 71卷 / 01期
关键词：
1,3-dipolar cycloadditions; azomethine ylides; aziridines; 1,3-thiazole-5(4H)-thiones; crystal structure; synthesis;
D O I：
暂无
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An azomethine ylide, generated in situ by thermal ring opening of cis-1-methyl-2,3-diphenylaziridine (3), undergoes a smooth cycloaddition onto the C=S bond of 1,3-thiazole-5(4H)-thiones 1 to give the stereoisomeric spiro-thiazolidines 4 and 5. The trans-configuration of the phenyl substituents in both cycloadducts was established by X-ray crystallography.
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页码：32 / 39
页数：8
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Kutyashev, Igor B. ;
Ulitko, Maria, V ;
Barkov, Alexey Yu ;
Zimnitskiy, Nikolay S. ;
Korotaev, Vladislav Yu ;
Sosnovskikh, Vyacheslav Ya .
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[42]   Regio- and Stereoselective 1,3-dipolar Cycloaddition of Azomethine Ylides Based on Isatins and (thia)proline to 3-nitro-2-(trifluoro(trichloro)methyl)-2H-chromenes: Synthesis and Cytotoxic Activity of 6-(trihalomethyl)-spiro[chromeno(thia)pyrrolizidine-11,3'-indolin]-2'-ones [J].
Igor B. Kutyashev ;
Maria V. Ulitko ;
Alexey Yu. Barkov ;
Nikolay S. Zimnitskiy ;
Vladislav Yu. Korotaev ;
Vyacheslav Ya. Sosnovskikh .
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Alekseeva, Kseniia A. ;
Raspertov, Pavel, V ;
Celikesir, Sevim Turktekin ;
Akkurt, Mehmet ;
Toze, Flavien A. A. ;
Sorokina, Elena A. .
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2019, 75 :460-+
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Poornachandran, Mahalingam ;
Jayagobi, Mathesan ;
Raghunathan, Raghavachary .
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Moggach, Stephen A. ;
Skelton, Brian W. ;
Foster, Daven J. .
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Matsulevich, Zhanna, V ;
Lukiyanova, Julia M. ;
Naumov, Vladimir, I ;
Borisova, Galina N. ;
Osmanov, Vladimir K. ;
Borisov, Alexander, V ;
Grishina, Maria M. ;
Khrustalev, Victor N. .
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2019, 75 :675-+
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