Fused tetracyclic heterocycles by thermally initiated intramolecular criss-cross cycloaddition of 3-substituted homoallenylazines
| Title in English | Fused tetracyclic heterocycles by thermally initiated intramolecular criss-cross cycloaddition of 3-substituted homoallenylazines. |
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| Authors | |
| Year of publication | 2005 |
| Type | Article in Periodical |
| Magazine / Source | European Journal of Organic Chemistry |
| MU Faculty or unit | |
| Citation | |
| Field | Organic chemistry |
| Keywords | allenes; cycloaddition; nitrogen heterocycles; sigmatropic rearrangement; polycycles |
| Description | A thermally initiated intramolecular criss-cross cycloaddition of 3-substituted symmetrical homoallenyl azines (5) was searched. Their cyclization led to interesting new fused heterocyclic systems consisting of four five-membered rings with two nitrogen heteroatoms (6). The preparation of azines was based on application of homoallenylaldehydes (4) in reaction with hydrazine. The homoallenylaldehydes (4) were prepared by Claisen rearrangement of new N,N-disubstituted 4-[(2-methylprop-1-en-1-yl)oxy]but-2-yn)-1-amines (3a-f) prepared by Mannich reaction from 2-methylprop-1-en-1-yl prop-2-yn-1-yl ether (2). The success in the reaction was based on improved solventless procedure of 1-chloro-2-methylpropyl prop-2-yn-1-yl ether (1) synthesis and its conversion to fully isolable 2-methylprop-1-en-1-yl prop-2-yn-1-yl ether (2) in high yield. |
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