126215-93-8Relevant articles and documents
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,
1,3-OXAZINES AS BACE 1 AND/OR BACE2 INHIBITORS
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Page/Page column 68, (2012/12/13)
The present invention provides compounds of formula I having BACE1 and/or BACE2 inhibitory activity, their manufacture, pharmaceutical compositions containing them and their use as therapeutically active substances. The active compounds of the present inv
INTRAMOLECULAR DIELS-ALDER REACTIONS OF 2-(ALKYNYL)PYRIMIDINES AND 2-(ALKYNYL)PYRIDINES
Frissen, A. E.,Marcelis, A. T. M.,Geurtsen, G.,Bie, D. A. de,Plas, H. C. van der
, p. 5151 - 5162 (2007/10/02)
Pyrimidines 3,7 and 13 carrying an ο-alkynyl side-chain -CR2(CH2)nCH2CCH (R=H, CN; n=1,2) at the 2-position undergo intramolecular inverse electron demand Diels-Alder reactions across the C-2 and C-5 positions.Loss of hydrogen cyanide, caused by a retro-Diels-Alder reaction, from the intermediate cycloadducts leads to annelated pyridines 5,9 and 15, respectively.Similarly, from the nitropyridines 16 the 2,3-dihydronitro-1H-indenes 18 are obtained.The influence of electronic and steric effects on the rate of cycloaddition is discussed.Gem-disubstitution on the chain connecting the reaction centers leads to a considerable rate enhancement for compounds 3 vs 13.Compounds 7, having an extra methylene group in the tether between diene and dienophile, react much slower than compounds 3 due to decreased entropic assistance.