Study on selectivity in the reaction of 2-substituted pyridinium-N-imines with dimethyl acetylenedicarboxylate

Study on selectivity in the reaction of 2-substituted pyridinium-N-imines with dimethyl acetylenedicarboxylate

[Display omitted] Reactions of 2-X-pyridinium-N-imines (X=F, Cl, Br, CN, OPh, NH2, N-morpholine) with dimethyl acetylenedicarboxylate (DMAD) have been studied. In the case of X=Cl, Br, CN, OPh both 7-substituted- and 7-H-pyrazolo[1,5-a]pyridines are formed. The 7-H/7-X ratio usually increases with t...

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Veröffentlicht in:Tetrahedron letters 2016-03, Vol.57 (10), p.1093-1096
Hauptverfasser: Supranovich, Vyacheslav I., Vorob’ev, Aleksey Yu, Borodkin, Gennady I., Gatilov, Yury V., Shubin, Vyacheslav G.
Format: Artikel
Sprache:eng
Schlagworte:
1,3-Dipolar cycloaddition
C–X bond cleavage
DFT calculations
Dimethyl
N-Amine salts
Polarity
Pyrazolo[1,5-a]pyridines
Selectivity
Solvents
Tetrahedrons
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Zusammenfassung:[Display omitted] Reactions of 2-X-pyridinium-N-imines (X=F, Cl, Br, CN, OPh, NH2, N-morpholine) with dimethyl acetylenedicarboxylate (DMAD) have been studied. In the case of X=Cl, Br, CN, OPh both 7-substituted- and 7-H-pyrazolo[1,5-a]pyridines are formed. The 7-H/7-X ratio usually increases with the growing solvent polarity. The reaction of N-amino-2-iminopyridine with DMAD gives substituted pyrido[1,2-b][1,2,4]triazine.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2016.01.092