TY - JOUR
T1 - A novel oxidative free radical reaction between 2-amino-1,4-benzoquinones and benzoylacetonitriles
AU - Chuang, Che Ping
AU - Tsai, An I.
N1 - Funding Information:
We are grateful to the National Science Council of the ROC for financial support (Grant no. NSC-92-2113-M-006-008).
Copyright:
Copyright 2008 Elsevier B.V., All rights reserved.
PY - 2007/9/24
Y1 - 2007/9/24
N2 - The manganese(III) initiated oxidative free radical reaction between 2-amino-1,4-benzoquinones and benzoylacetonitriles is described. This free radical reaction provides a novel method for the synthesis of spirodione 3 and spirolactone 4. With 5,6-dimethyl-2-methylamino-1,4-benzoquinone, spirodione 3 was obtained exclusively. On the contrary, with 5-methyl-2-methylamino-1,4-benzoquinone, spirolactone 4 was produced in high chemo- and regioselectivity. By heating with sodium acetate, spirodione 3 can be converted to 4 effectively.
AB - The manganese(III) initiated oxidative free radical reaction between 2-amino-1,4-benzoquinones and benzoylacetonitriles is described. This free radical reaction provides a novel method for the synthesis of spirodione 3 and spirolactone 4. With 5,6-dimethyl-2-methylamino-1,4-benzoquinone, spirodione 3 was obtained exclusively. On the contrary, with 5-methyl-2-methylamino-1,4-benzoquinone, spirolactone 4 was produced in high chemo- and regioselectivity. By heating with sodium acetate, spirodione 3 can be converted to 4 effectively.
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U2 - 10.1016/j.tet.2007.07.008
DO - 10.1016/j.tet.2007.07.008
M3 - Article
AN - SCOPUS:34547765857
VL - 63
SP - 9712
EP - 9717
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 39
ER -