Rearrangement of fused tetracyclic heterocycles induced by alkyl halides and formation of a new type of "proton sponge"

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14310%2F09%3A00049585" target="_blank" >RIV/00216224:14310/09:00049585 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1016/j.tet.2008.11.057" target="_blank" >http://dx.doi.org/10.1016/j.tet.2008.11.057</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.tet.2008.11.057" target="_blank" >10.1016/j.tet.2008.11.057</a>

Result language
angličtina
Original language name
Rearrangement of fused tetracyclic heterocycles induced by alkyl halides and formation of a new type of "proton sponge"
Original language 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.
Czech name
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Czech description
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Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Project
<a href="/en/project/GA203%2F09%2F1345" target="_blank" >GA203/09/1345: Allenyl synthon in synthesis of heterocyclic compounds</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2009
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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