Journal of Organic Chemistry p. 5057 - 5064 (1980)
Update date:2022-08-04
Topics:
Moore, Harold W.
Sing, Yuen-Lung L
Sidhu, Ravinder S.
Synthetic methodology is presented which allows the facile synthesis of 2,5-disubstituted 1,4-benzoquinones.This involves the initial 1,2-addition of an alkynyllithium reagent to one of the carbonyl groups of 2,5-diethoxy- or 2,5-dichloro-3,6-dimethoxy-1,4-benzoquinone.This is followed by an analogous addition of an alkyl-, aryl-, or alkynyllithium to the remaining carbonyl to give a cyclohexa-2,5-diene-1,4-diol derivative.Acid hydrolysis of these adducts results in the 2,5-dialkylated 1,4-benzoquinones.This methodology was employed to prepare 7-chloro-6-methyl-1,2,5,8-tetrahydro-3H-pyrrolo<1,2-α>indole-5,8-dione (14), a compound having the basic ring systeme of the mitomycin antineoplastic antibiotics.
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Doi:10.1002/jhet.5570170557
(1980)Doi:10.1016/S0040-4020(01)92366-X
(1981)Doi:10.1023/B:RUBI.0000015776.60923.96
(2004)Doi:10.1039/c4ra17090c
(2015)Doi:10.1021/ol052214x
(2005)Doi:10.1021/ja056334b
(2006)