Rearrangement of fused tetracyclic heterocycles induced by alkyl halides and formation of a new type of ‘proton sponge’
@article{Zachov2009RearrangementOF, title={Rearrangement of fused tetracyclic heterocycles induced by alkyl halides and formation of a new type of ‘proton sponge’}, author={Hana Zachov{\'a} and S. Man and J. Taraba and M. Pot{\'a}{\vc}ek}, journal={Tetrahedron}, year={2009}, volume={65}, pages={792-797} }
Abstract 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… CONTINUE READING
17 Citations
Substituted homoallenyl aldehydes and their derivatives. Part 1: Homoallenyl aldehydes and protected hydrazones
- Chemistry
- Chemical Papers
- 2012
- 2
Ultrasound-promoted synthesis of novel fused heterocycles by criss-cross cycloaddition
- Chemistry
- 2016
- 9
- PDF
Substituted diazatetracyclo[4.4.0.1(3,10).1(5,8)]dodecanes as stable caged proton sponges.
- Chemistry, Medicine
- The Journal of organic chemistry
- 2012
- 10
Molecular design of organic superbases, azacalix[3](2,6)pyridines: catalysts for 1,2- and 1,4-additions.
- Chemistry, Medicine
- The Journal of organic chemistry
- 2012
- 12
Novel and selective synthesis of unsymmetrical azine derivatives via a mild reaction
- Chemistry
- Monatshefte für Chemie - Chemical Monthly
- 2013
- 10
- PDF
Substituted homoallenyl aldehydes and their derivatives. Part 2: Azines
- Chemistry
- Chemical Papers
- 2012
- 3
Superbasic alkyl-substituted bisphosphazene proton sponges: synthesis, structural features, thermodynamic and kinetic basicity, nucleophilicity and coordination chemistry.
- Chemistry, Medicine
- Chemistry
- 2014
- 29
References
SHOWING 1-10 OF 15 REFERENCES
A new rearrangement of fused tetracyclic heterocycles in an acidic medium in the presence of NaBH3CN
- Chemistry
- 2006
- 6
Fused Tetracyclic Heterocycles by Thermally Initiated Intramolecular Criss-Cross Cycloaddition of 3-Substituted Homoallenylaldazines
- Chemistry
- 2005
- 22
New Proton‐Sponge‐Like Macrocyclic Compound: Synergistic Hydrogen Bonds of Aminopyridine
- Chemistry
- 2006
- 19
Design of C2-chiral diamines that are computationally predicted to be a million-fold more basic than the original proton sponges.
- Chemistry, Medicine
- Journal of the American Chemical Society
- 2005
- 46
Rational design and first principles studies toward the discovery of a small and versatile proton sponge.
- Chemistry, Medicine
- Angewandte Chemie
- 2006
- 20
- PDF