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.
Synthesis of annulated pyridines by intramolecular inverse-electron-demand hetero-diels-alder reaction under superheated continuous flow conditions
Martin, Rainer E.,Morawitz, Falk,Kuratli, Christoph,Alker, Andre M.,Alanine, Alexander I.
supporting information; experimental part, p. 47 - 52 (2012/01/14)
Pyrimidine alkynes can be transformed into the corresponding annulated pyridines efficiently in flow. The superheating of organic solvents far beyond their boiling point enables toxic and difficult to workup solvents such as nitrobenzene or chlorobenzene,
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.
RING-TRANSFORMATIONS OF PYRIMIDINES BY INTRAMOLECULAR DIELS-ALDER REACTIONS. SYNTHESIS OF ANNELATED PYRIDINES
Frissen, A. E.,Marcelis, A. T. M.,Plas, H. C. van der
, p. 803 - 812 (2007/10/02)
Pyrimidines carrying an ω-alkyne side-chain -XCH2CH2CCH (X=O,N,S,SO,SO2) at the 2 or 5 position undergo intramolecular inverse electron demand Diels-Alder reactions across the C-2 and C-5 positions; elimination of hydrogen (or alkyl) cyanide from the intermediate adducts leads to condensed pyridines.The influence of the hetero atom (X) in the dienophilic side-chain and that of substituents in the pyrimidine ring on the reactivity is discussed.
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
