111097-47-3Relevant articles and documents
Intramolecular Inverse Electron-Demand [4 + 2] Cycloadditions of Ynamides with Pyrimidines: Scope and Density Functional Theory Insights
Duret, Guillaume,Quinlan, Robert,Yin, Boyang,Martin, Rainer E.,Bisseret, Philippe,Neuburger, Markus,Gandon, Vincent,Blanchard, Nicolas
, p. 1726 - 1742 (2017)
4-Aminopyridines are valuable scaffolds for the chemical industry in general, from life sciences to catalysis. We report herein a collection of structurally diverse polycyclic fused and spiro-4-aminopyridines that are prepared in only three steps from commercially available pyrimidines. The key step of this short sequence is a [4 + 2]/retro-[4 + 2] cycloaddition between a pyrimidine and an ynamide, which constitutes the first examples of ynamides behaving as electron-rich dienophiles in [4 + 2] cycloaddition reactions. In addition, running the ihDA/rDA reaction in continuous mode in superheated toluene, to overcome the limited scalability of MW reactions, results in a notable production increase compared to batch mode. Finally, density functional theory investigations shed light on the energetic and geometric requirements of the different steps of the ihDA/rDA sequence.
TRICYCLIC COMPOUND AND MEDICAL USE THEREOF
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Page/Page column 63, (2009/09/28)
The present invention provides a compound represented by the formula wherein R1 is a hydrocarbon group optionally having substituent(s), amino optionally having substituent(s), hydroxy optionally having a substituent or a heterocyclic group optionally having substituent(s), R2 is a hydrogen atom or a hydrocarbon group optionally having substituent(s), R3 is a hydrogen atom, a halogen atom, a hydrocarbon group optionally having substituent(s), amino optionally having substituent(s), hydroxy optionally having a substituent or mercapto optionally having a substituent, Xa to Xe are each a carbon atom or a nitrogen atom, m is 0 to 2, and ring A to ring C are each a ring optionally having substituent(s), or a salt thereof, which is useful as an agent for the prophylaxis or treatment of a disease relating to an action of melatonin, and the like.
NOVEL INTRAMOLECULAR DIELS-ALDER REACTIONS OF PYRIMIDINES. SYNTHESIS OF HETEROCYCLIC ANNELATED PYRIDINES
Frissen, August E.,Marcelis, Antonius T. M.,Plas, Henk C. van der
, p. 1589 - 1592 (2007/10/02)
Pyrimidines carrying a dienophilic side-chain at the 2 or 5 position undergo intramolecular Diels-Adler reactions to give heterocyclic annelated pyridines