Publication:
5-Alkenylthiazoles as In-Out Dienes in Polar [4+2] Cycloaddition Reactions

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13EJOC7500.pdf(960.71 KB)
Date
2013-09-25
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Authors
Alajarín, Mateo ; Cabrera, Jose ; Sanchez-Andrada, Pilar ; Bautista, Delia ; Pastor Vivero, Aurelia
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Publisher
Wiley
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publication.page.department
Química Orgánica
DOI
10.1002/ejoc.201300925
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info:eu-repo/semantics/article
Description
Abstract
5-Alkenyl-2-aminothiazoles react as in-out dienes with a wide range of electron-poor dienophiles leading to the corresponding cycloaddition products in good to excellent yields. The [4+2] cycloadditions of 5-alkenyl-2-aminothiazoles can be classified as site-selective since only the diene moiety including the formal C-C double bond of the heterocycle and that of the side-chain is involved. Calculations of the HOMO energy values of representative 5-alkenyl-2-aminothiazoles are disclosed The cycloadditions are endo-selective with N-phenylmaleimide or maleic anhydride and regioselective when the reactions are conducted with non symmetrical dienophiles. Completely oxidized cycloadducts are obtained in the reactions of 5-alkenyl-2-aminothiazoles with naphthoquinone or DMAD. Unexpectedly, the reactions with PTAD are not stereospecific. A mechanism placed at the concerted/stepwise boundary is proposed.
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Synthetic methods , Cycloaddition , Cyclization , Zwitterions , Reaction mechanism , Nitrogen heterocycles
Citation
European Journal Organic Chemistry, 2013, 7500–7511
URI
http://hdl.handle.net/10201/113645
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