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| Content Provider | World Health Organization (WHO)-Global Index Medicus |
|---|---|
| Author | Jochmann, Phillip Spaniol, Thomas P. Leich, Valeri Okuda, Jun |
| Description | Author Affiliation: Jochmann P ( Institute of Inorganic Chemistry, RWTH Aachen University, Landoltweg 1, 52056 Aachen, Germany.) |
| Abstract | A facile and general synthetic pathway for the production of dearomatized, allylated, and CH bond activated pyridine derivatives is presented. Reaction of the corresponding derivative with the previously reported reagent bis(allyl)calcium, $[Ca(C_{3}H_{5})_{2}]$ (1), cleanly affords the product in high yield. The range of N-heterocyclic compounds studied comprised 2-picoline (2), 4-picoline (3), 2,6-lutidine (4), 4-tert-butylpyridine (5), 2,2′-bipyridine (6), acridine (7), quinoline (8), and isoquinoline (9). Depending on the substitution pattern of the pyridine derivative, either carbometalation or CH bond activation products are obtained. In the absence of methyl groups ortho or para to the nitrogen atom, carbometalation leads to dearomatized products. $C(sp^{3})H$ bond activation occurs at ortho and para situated methyl groups. Steric shielding of the 4-position in pyridine yields the ring-metalated product through $C(sp^{2})H$ bond activation instead. The isolated compounds $[Ca(2-CH_{2}-C_{5}H_{4}N)_{2}(THF)]$ (2 b⋅(THF)), $[Ca(4-CH_{2}-C_{5}H_{4}N)_{2}(THF)_{2}]$ $(3 b⋅(THF)_{2}),$ $[Ca(2-CH_{2}-C_{5}H_{3}N-6-CH_{3})_{2}(THF)_{n}]$ $(4 b⋅(THF)_{n};$ n=0, 0.75), $[Ca\{2-C_{5}H_{3}N-4-C(CH_{3})_{3}\}_{2}(THF)_{2}]$ $(5 c⋅(THF)_{2}),$ $[Ca\{4,4′-(C_{3}H_{5})_{2}-(C_{10}H_{8}N_{2})\}(THF)]$ (6 a⋅(THF)), $[Ca(NC_{13}H_{9}-9-C_{3}H_{5})_{2}(THF)]$ (7 a⋅(THF)), $[Ca(4-C_{3}H_{5}-C_{9}H_{7}N)_{2}(THF)]$ (8 b⋅(THF)), and $[Ca(1-C_{3}H_{5}-C_{9}H_{7}N)_{2}(THF)_{3}]$ $(9 a⋅(THF)_{3})$ have been characterized by NMR spectroscopy and metal analysis. $9 a⋅(THF)_{4}$ and $4 b⋅(THF)_{3}$ were additionally characterized in the solid state by X-ray diffraction experiments. $4 b⋅(THF)_{3}$ shows an aza-allyl coordination mode in the solid state. Based on the results, mechanistic aspects are discussed in the context of previous findings. |
| ISSN | 09476539 |
| e-ISSN | 15213765 |
| Journal | Chemistry - A European Journal |
| Issue Number | 43 |
| Volume Number | 17 |
| Language | English |
| Publisher | Wiley-VCH;ChemPubSoc Europe |
| Publisher Date | 2011-10-17 |
| Publisher Place | Germany |
| Access Restriction | Open |
| Subject Keyword | Acridines Chemistry Alkylating Agents Calcium Isoquinolines Picolines Pyridines Alkylation Hydrogen Bonding Magnetic Resonance Spectroscopy Research Support, Non-U.S. Gov't |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |
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