PÍŽOVÁ, Hana, Stanislav MAN, Jan TARABA and Milan POTÁČEK. Rearrangement of fused tetracyclic heterocycles induced by alkyl halides and formation of a new type of "proton sponge". Tetrahedron. Elsevier Science Ltd., 2009, vol. 65, No 4, p. 792-797. ISSN 0040-4020. Available from: https://dx.doi.org/10.1016/j.tet.2008.11.057. |
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@article{800666, author = {Pížová, Hana and Man, Stanislav and Taraba, Jan and Potáček, Milan}, article_number = {4}, doi = {http://dx.doi.org/10.1016/j.tet.2008.11.057}, keywords = {tetracyclic fused heteocycles; rearrangement; alkyl halides initiation; proton sponge;}, language = {eng}, issn = {0040-4020}, journal = {Tetrahedron}, title = {Rearrangement of fused tetracyclic heterocycles induced by alkyl halides and formation of a new type of "proton sponge"}, volume = {65}, year = {2009} }
TY - JOUR ID - 800666 AU - Pížová, Hana - Man, Stanislav - Taraba, Jan - Potáček, Milan PY - 2009 TI - Rearrangement of fused tetracyclic heterocycles induced by alkyl halides and formation of a new type of "proton sponge" JF - Tetrahedron VL - 65 IS - 4 SP - 792-797 EP - 792-797 PB - Elsevier Science Ltd. SN - 00404020 KW - tetracyclic fused heteocycles KW - rearrangement KW - alkyl halides initiation KW - proton sponge; N2 - 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. ER -
PÍŽOVÁ, Hana, Stanislav MAN, Jan TARABA and Milan POTÁČEK. Rearrangement of fused tetracyclic heterocycles induced by alkyl halides and formation of a new type of ''proton sponge''. \textit{Tetrahedron}. Elsevier Science Ltd., 2009, vol.~65, No~4, p.~792-797. ISSN~0040-4020. Available from: https://dx.doi.org/10.1016/j.tet.2008.11.057.
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