4-Methylpyrimidinium ylides. Part 7: 3+2 Dipolar cycloadditions to non-symmetrical substituted alkenes and alkynes |
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Authors: | Ionel I Mangalagiu Geanina C MangalagiuCalin Deleanu Gabi DrochioiuMagda Ghe Petrovanu |
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Affiliation: | Department of Organic Chemistry, ‘Al. I. Cuza’ University, B-dul Copou-11, 6600 Iasi, Romania |
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Abstract: | The ability of 4-methylpyrimidinium ylides (as 1,3-dipoles) to react with activated non-symmetrical substituted dipolarophiles (alkenes and alkynes) is presented. 4-Methylpyrimidinium ylides did not react with alkenes. With alkynes the reactions are regiospecific, a single regioisomer being obtained. A possible mechanism for the reaction pathway is proposed. For the first time in the pyrimidinium ylides series both isomers resulting from bonding to the 2-and 6-positions of the heterocycle ring were obtained. The appropriate conditions in order to increase the selectivity of one of the isomers were determined. |
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Keywords: | pyrimidinium ylides regioselectivity azabicyclic compounds |
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