| PÍŽOVÁ, Hana, Stanislav MAN, Jan TARABA a Milan POTÁČEK. Rearrangement of fused tetracyclic heterocycles induced by alkyl halides and formation of a new type of "proton sponge". Tetrahedron. Elsevier Science Ltd., roč. 65, č. 4, s. 792-797. ISSN 0040-4020. doi:10.1016/j.tet.2008.11.057. 2009. |
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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 a 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., roč.~65, č.~4, s.~792-797. ISSN~0040-4020. doi:10.1016/j.tet.2008.11.057. 2009.
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