Synthesis of condensed heterocycles via cyclopropylimine rearrangement of cyclopropylazoles
β Scribed by Yury V. Tomilov; Dmitry N. Platonov; Aleksandr E. Frumkin; Dmitry L. Lipilin; Rinat F. Salikov
- Publisher
- Elsevier Science
- Year
- 2010
- Tongue
- French
- Weight
- 473 KB
- Volume
- 51
- Category
- Article
- ISSN
- 0040-4039
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π SIMILAR VOLUMES
N-Cyclopropylimines rearrange under thermal conditions to give 1-pyrrolines. The effect of imine and cyclopropane substitution is explored. This methodology allows the presence of different substituents (alkyl, alkenyl, aryl) and the reaction proceeds regiospecifically.
Dimerizations of cyclic enamines 1 (R=H2) occurring via iminium intermediates 2 (R=H2) are well-known 1) and have been applied recently in alkaloid synthe-sis2). Schematically the overall process can be represented as follows: R'