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Synfacts 2011(3): 0262-0262
DOI: 10.1055/s-0030-1259575
DOI: 10.1055/s-0030-1259575
Synthesis of Heterocycles
© Georg Thieme Verlag
Stuttgart ˙ New York
One-Pot Synthesis of Indolizines from Pyridines, Benzyl Halides, and Alkenes
H. Hu*, K. Shi, R. Hou, Z. Zhang, Y. Zhu, J. Zhoua
Huaiyin Normal University, Huaian, P. R. of China
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
16. Februar 2011 (online)
Significance
Reported is the synthesis of 3-arylindolizines 5 from pyridines 1, benzyl halides 2 and electron-deficient dihaloalkenes 4 via a one-pot alkylation-1,3-dipolar cycloaddition strategy. Both EDGs and EWGs are tolerated on the benzyl halide fragment. However, substrates bearing substituents ortho to the pyridine nitrogen (2-methylpyridine, 2-bromopyridine, quinoline) failed to give any of the desired indolizines. The reaction is tolerant of a wide range of dihaloalkenes, giving rise to indolizines 6-9 in moderate yields.