Synthesis of densely substituted pyridine derivatives from nitriles by a non-classical [4+2] cycloaddition/1,5-hydrogen shift strategy
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Abstract A novel strategy has been established to assemble an array of densely substituted pyridine derivatives from nitriles and o-substituted aryl alkynes or 1-methyl-1,3-enynes via a non-classical [4 + 2] cycloaddition along with 1,5-hydrogen shift process. The well-balanced affinities of two different alkali metal salts enable the C(sp3)-H bond activation as well as the excellent chemo- and regioselectivities. This protocol offers a new guide to construct pyridine frameworks from nitriles with sp3-carbon pronucleophiles, and shows potential applications in organic synthesis and medicinal chemistry.
1978 ◽
Vol 253
(5)
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pp. 1458-1464
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1978 ◽
Vol 253
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pp. 1451-1457
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1967 ◽
Vol 71
(12)
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pp. 3879-3887
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1999 ◽
Vol 67
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pp. 111-116
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2001 ◽
Vol 12
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pp. 574-582
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1979 ◽
Vol 101
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pp. 328-333
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1978 ◽
Vol 40
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pp. 697-698
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