Rearrangement of fused tetracyclic heterocycles induced by alkyl halides and formation of a new type of "proton sponge"
| Authors | |
|---|---|
| Year of publication | 2009 |
| Type | Article in Periodical |
| Magazine / Source | Tetrahedron |
| MU Faculty or unit | |
| Citation | |
| Doi | http://dx.doi.org/10.1016/j.tet.2008.11.057 |
| Field | Organic chemistry |
| Keywords | tetracyclic fused heteocycles; rearrangement; alkyl halides initiation; proton sponge; |
| Description | Intramolecular criss-cross cycloaddition of 3-substituted symmetrical homoallenyl azines 2 by heating in xylene lead to interesting fused heterocyclic systems consisting of four five-membered rings with two nitrogen atoms in the skeleton 3. These compounds 3 were found to be sensitive to attack by alkyl halides. Their presence, depending on the reaction conditions, resulted in a new type of rearrangement leading to compounds 4 and 5, respectively. With an excess of alkyl halide and in the presence of NaBH3CN a new structure 6 with signs of the molecule corresponding a proton sponge moiety was created. The scope of the rearrangement and reaction products structure was investigated. |
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