Sauer, Juergen and Heldmann, Dieter K. and Pabst, Gunther R. (1999) From 1,2,4-triazines and tributyl(ethynyl)tin to stannylated bi- and terpyridines: The cycloaddition pathway. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (1). pp. 313-321. ISSN 1434-193X, 1099-0690
Full text not available from this repository. (Request a copy)Abstract
Recently, we reported on cycloadditions between electron-deficient heterodienes and tributyl(ethynyl)tin, which provide a new pathway to stannylated pyridazines and, in one special case, pyridines. In order to broaden the synthetic scope of these reactions, we have developed hetero [4+2] cycloaddition reactions between a number of tailor-made 1,2,4-triazines 5-9 (acting as heterodienes), and tributyl(ethynyl)tin (acting as dienophile). The desired 1,2,4-triazines are readily available, in moderate to very good yields, by the condensation reactions of appropiate carbamidrazones and glyoxals. These cycloadditions open up a novel route to regiospecifically stannylated 2,2'-bi- and 2,2',6',2 "-terpyridines 1-4, 11 in good yields. The stannanes 1-4, 11 are versatile synthetic intermediates, and with this strategy various substituents can be incorporated directly by substitution of the stannyl group, as was shown for halogens and carbon electrophiles under Stille conditions.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | TRANSITION-METAL COMPLEXES; 2,2'-BIPYRIDINES; SENSORS; cycloadditions; cross-coupling; halogens; nitrogen heterocycles; tin |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 29 Nov 2022 13:19 |
| Last Modified: | 29 Nov 2022 13:19 |
| URI: | https://pred.uni-regensburg.de/id/eprint/48647 |
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