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
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.
引用
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页码:32 / 39
页数:8
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[21]   A strategic approach to the synthesis of novel class of dispiroheterocyclic derivatives through 1,3 dipolar cycloaddition of azomethine ylide with (E)-3-arylidene-2,3-dihydro-8-nitro-4-quinolone [J].
Chandraprakash, Kumarasamy ;
Sankaran, Mathan ;
Uvarani, Chokalingam ;
Shankar, Ramasamy ;
Ata, Athar ;
Dallemer, Frederic ;
Mohan, Palathurai Subramaniam .
TETRAHEDRON LETTERS, 2013, 54 (29) :3896-3901
[22]   1,3-Dipolar Cycloaddition of Nitrile Imines with Functionalized Acetylenes: Regiocontrolled Sc(OTf)3-Catalyzed Synthesis of 4-and 5-Substituted Pyrazoles [J].
Bonini, Bianca Flavia ;
Franchini, Mauro Comes ;
Gentili, Denis ;
Locatelli, Erika ;
Ricci, Alfredo .
SYNLETT, 2009, (14) :2328-2332
[23]   Imposed hydrophobic interactions by NaCl: accountable attribute for the synthesis of spiro-[acenaphthylene-1,5′-pyrrolo[1,2-c]thiazole] derivatives via 1,3-dipolar cycloaddition reaction in aqueous medium [J].
Dandia, Anshu ;
Parewa, Vijay ;
Kumari, Sukhbeer ;
Bansal, Sarika ;
Sharma, Amit .
GREEN CHEMISTRY, 2016, 18 (08) :2488-2499
[24]   Crystal structure of 2-methyl-4-[(thiophen-2-yl)methylidene]-1,3-oxazol-5(4H)-one [J].
Sharma, Preetika ;
Subbulakshmi, K. N. ;
Narayana, B. ;
Byrappa, K. ;
Kant, Rajni .
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2015, 71 :O123-U556
[25]   Silver-Catalyzed Diastereo- and Enantioselective Michael Addition and 1,3-Dipolar Cycloaddition Reactions of Imino Esters to 3-Methyl-4-nitro-5-styrylisoxazoles [J].
Kato, Shuma ;
Suzuki, Yuko ;
Suzuki, Kota ;
Haraguchi, Ryosuke ;
Fukuzawa, Shin-ichi .
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (22) :13965-13972
[26]   Crystal and molecular structures of [(2-amino-5-methyl-1,3-thiazole)(1,4,7-triazaheptane)copper(II)] dinitrate [J].
Bolos, CA ;
Fanourgakis, PV ;
Christidis, PC ;
Nikolov, GS .
POLYHEDRON, 1999, 18 (11) :1661-1668
[27]   Stereoselective synthesis of cis- and trans-2′,5′-disubstituted N-arylpyrrolo[3′,4′:1,9](C60-Ih)[5,6]fullerenes by the 1,3-dipolar cycloaddition of azomethine ylides from dialkyl aziridinedicarboxylates to fullerene C60 [J].
A. S. Konev ;
A. A. Mitichkina ;
A. F. Khlebnikov ;
H. Frauendorf .
Russian Chemical Bulletin, 2012, 61 :863-870
[28]   Synthesis of Spiro[imidazole-4,3′-pyrrolo[1,2-a]quinolin]-5-ones via 1,3-Dipolar Cycloaddition of Quinolinium Ylides with Arylydeneimidazol-4-ones [J].
Molchanova, Marina V. ;
Ikonnikova, Viktoria A. ;
Smirnov, Alexander Yu. ;
Solyev, Pavel N. ;
Baranov, Mikhail S. ;
Mikhaylov, Andrey A. .
CHEMISTRYSELECT, 2024, 9 (08)
[29]   Stereoselective synthesis of oxazolidine, hexahydropyrrolo [2,1-b] oxazole, and tetrahydro-2H-oxazolo [3,2-c] thiazole grafted macrocycles through intramolecular 1,3-dipolar cycloaddition reaction [J].
Purushothaman, S. ;
Raghunathan, R. .
TETRAHEDRON LETTERS, 2009, 50 (49) :6848-6850
[30]   4-(N,N-Dimethylamino)pyridine (DMAP)-Catalyzed 1,3-Dipolar Cycloaddition of 3-Aminooxindole-Based Azomethine Ylides with ,-Unsaturated Acyl Phosphonates for the Construction of Spiropyrrolidinyl-2,3-oxindoles [J].
He, Jin ;
Sun, Rong-Guo ;
Fan, Li ;
Tian, Shi-Yan ;
Huang, Ting-Ping ;
Chen, Zhuo ;
Chen, Lin .
SYNTHESIS-STUTTGART, 2019, 51 (06) :1353-1364