No.126
Direct Cyanomethylation of Nitroarenes
| P1602 | (Phenylthio)acetonitrile (1) |
5g |
(Phenylthio)acetonitrile (1) can react with nitroarenes and introduce a cyanomethyl group at the ortho- or para- position to the nitro group.1 The resulting o-nitroarylacetonitrile 2, for example, is a useful starting material for the synthesis of nitrogen-containing fused ring compounds.2
References
1) Vicarious substitution of hydrogen in aromatic nitro compounds
a) M. Makosza, A. Kinowski, W. Danikiewicz, B. Mudryk, Liebigs Ann. Chem., 1986, 69.
b) M. Makosza, J. Winiarski, J. Org. Chem., 1980, 45, 1534.
c) M. Makosza, J. Winiarski, J. Org. Chem., 1984, 49, 1494.
2) The synthesis of N-containing fused ring compounds
a) M. Vlachou, A. Tsotinis, L. R. Kelland, D. E. Thurston, Heterocycles, 2002, 57, 129.
b) Z. Wroel, Synthesis, 1997, 753.
a) M. Makosza, A. Kinowski, W. Danikiewicz, B. Mudryk, Liebigs Ann. Chem., 1986, 69.
b) M. Makosza, J. Winiarski, J. Org. Chem., 1980, 45, 1534.
c) M. Makosza, J. Winiarski, J. Org. Chem., 1984, 49, 1494.
2) The synthesis of N-containing fused ring compounds
a) M. Vlachou, A. Tsotinis, L. R. Kelland, D. E. Thurston, Heterocycles, 2002, 57, 129.
b) Z. Wroel, Synthesis, 1997, 753.
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