Unexpected Heterocyclic Products from Cycloaddition Reactions of Nonsymmetrical Allenyl Aldoketazines with Substituted Alkynes
@article{Galeta2011UnexpectedHP, title={Unexpected Heterocyclic Products from Cycloaddition Reactions of Nonsymmetrical Allenyl Aldoketazines with Substituted Alkynes}, author={J. Galeta and S. Man and Jean-Philippe Bouillon and M. Pot{\'a}{\vc}ek}, journal={European Journal of Organic Chemistry}, year={2011}, volume={2011}, pages={392-398} }
Thermally initiated cycloaddition reactions of nonsymmetrical allenyl azines 1 with alkynes or other dipolarophiles usually lead to compounds with three fused, five-membered heterocyclic rings. With alkynes with pronounced "push-pull" systems, however, the reaction ends with the formation of substituted pyrrolidino[1,2-b]pyrazoles 4 and, in the case of azines with trifluoromethyl substitution, ring opening leads to the isolation of compounds 9. Reaction mechanisms for these transformations are… CONTINUE READING
11 Citations
Homoallenyl azines in criss-cross cycloaddition reactions
- Chemistry
- Monatshefte für Chemie - Chemical Monthly
- 2012
- 1
Cascade cyclization, dipolar cycloaddition of azomethine imines for the synthesis of pyrazolidines.
- Chemistry, Medicine
- Organic & biomolecular chemistry
- 2011
- 16
Substituted homoallenyl aldehydes and their derivatives. Part 1: Homoallenyl aldehydes and protected hydrazones
- Chemistry
- Chemical Papers
- 2012
- 2
Asymmetric synthesis of α-alkenyl homoallylic primary amines via 1,2-addition of Grignard reagent to α,β-unsaturated phosphonyl imines.
- Chemistry, Medicine
- RSC advances
- 2013
- 5
- PDF
Substituted homoallenyl aldehydes and their derivatives. Part 2: Azines
- Chemistry
- Chemical Papers
- 2012
- 3
Application of Pd-Catalyzed Cross-Coupling Reactions in the Synthesis of 5,5-Dimethyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazoles that Inhibit ALK5 Kinase.
- Chemistry, Medicine
- The Journal of organic chemistry
- 2016
- 3
References
SHOWING 1-10 OF 21 REFERENCES
Non-symmetrical allenyl azines and their transformations leading to new heterocyclic skeletons
- Chemistry
- 2009
- 7
- PDF
Combined intra-intermolecular criss-cross cycloaddition of a new fluorinated unsymmetrical allenylazine with alkynes
- Chemistry
- 2004
- 9
Allenic Compounds and Isothiocyanates as Key Building Units in the Synthesis of Heterocycles
- Chemistry
- 2004
- 99
New fused heterocycles by combined intra-intermolecular criss-cross cycloaddition of nonsymmetrical azines ☆
- Chemistry
- 2002
- 18
Sugars, alkaloids, and heteroaromatics: exploring heterocyclic chemistry with alkoxyallenes.
- Chemistry, Medicine
- Accounts of chemical research
- 2009
- 246