Functionalized Imides by Regioselective Ozonation
| Autor: | Hans-Dietrich Stachel, Eduard Eckl, Sabine Jax, Hermann Poschenrieder, Kurt Polborn, Peter Mayer |
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| Rok vydání: | 2006 |
| Předmět: |
chemistry.chemical_classification
Ozonolysis Bicyclic molecule Stereochemistry Diazomethane Organic Chemistry Regioselectivity Cleavage (embryo) Biochemistry Aldehyde Catalysis Inorganic Chemistry chemistry.chemical_compound chemistry Drug Discovery Alkoxy group Physical and Theoretical Chemistry Lactone |
| Zdroj: | Helvetica Chimica Acta. 89:971-982 |
| ISSN: | 1522-2675 0018-019X |
| DOI: | 10.1002/hlca.200690101 |
| Popis: | Ozonations of alkoxy- and (acyloxy)-substituted alkylidene-lactams 1 and 5 or of the alkylidene-sultams 9 and 10 proceeded by regioselective cleavage of the exocyclic CC bonds (Schemes 1 and 2). These bonds are part of an enamide system and, therefore, possess considerable polarity as shown by 13C-NMR spectra. As a result, the partly known maleimides 3 and 6 or the ‘sulfonimides’ 11 were obtained. Compounds 3 and 11 reacted with diazomethane to give the highly reactive bicyclic derivatives 8 and 12, respectively. The cinnamylidene-lactames 16a,b were converted by selective ozonolysis mainly into the formylmethylene lactames 17a,b (Scheme 3). The amino-substituted aldehyde 20 bears a structural relationship to the lactone antibiotic basidalin 21a. The tendency of some donor-substituted maleimides to undergo [2 + 2] cycloadditions was assessed (Scheme 4). The configuration of the photodimers 22a,b and 24a,b was established by X-ray crystallography. |
| Databáze: | OpenAIRE |
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