Publication details
Homoallenyl azines in criss-cross cycloaddition reactions
| Authors | |
|---|---|
| Year of publication | 2013 |
| Type | Article in Periodical |
| Magazine / Source | Monatshefte fur Chemie |
| MU Faculty or unit | |
| Citation | |
| Web | http://link.springer.com/article/10.1007/s00706-012-0865-7 |
| Doi | http://dx.doi.org/10.1007/s00706-012-0865-7 |
| Field | Organic chemistry |
| Keywords | 1;3 Dipole; Dipolarophile ; Stereoselective synthesis; Heterocycles; Retro reactions |
| Description | Thermally initiated combined intra-intermolecular criss-cross cycloadditions of substituted nonsymmetrical allenyl azines with isocyanate or isothiocyanate dipolarophiles were investigated. Substituted 1,3,10-triazatricyclo[ 5.2.1.04,10]dec-6-en-2-ones or -dec-6-ene-2-thiones were obtained as the main products in moderate to very good yields. The thermal stabilities of the tricyclic adducts in reactions with the competing reactive dipolarophile dimethyl acetylenedicarboxylate were studied and are discussed. In some cases, substituted 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazoles were found as side products. This reaction showed high atomeconomy and in all caseswe observed the presence of one diastereoisomer and regioisomer only, which was clearly revealed by crystallographic analysis. |
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